Thermoluminescence and a New Organic Light-Emitting Diode (OLED) Based on Triplet−Triplet Fluorescence of the Trimethylenemethane (TMM) Biradical

The results of an investigation of the thermoluminescence (TL) and electroluminescence (EL) of arylated methylenecyclopropanes 1, systems whose photoinduced electron-transfer (PET) chemistry has been thoroughly studied, are described. In both the TL and EL experiments with 1, electronically excited...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 29; pp. 9032 - 9036
Main Authors Namai, Hayato, Ikeda, Hiroshi, Hoshi, Yosuke, Kato, Nobuyuki, Morishita, Yoshii, Mizuno, Kazuhiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.07.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Free Radicals - chemistry
Gamma Rays
Indicators and Reagents
Luminescence
Magnetic Resonance Spectroscopy
Physical Sciences
Science & Technology
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
OXIDATION
RECOMBINATION
ARYLMETHYL RADICALS
ELECTRON-TRANSFER
GROUND-STATE
PHOTOCHEMISTRY
RADICAL-ION PAIRS
POTENTIALS
CYCLIZATION
SINGLET
Online AccessGet full text

Cover

Abstract The results of an investigation of the thermoluminescence (TL) and electroluminescence (EL) of arylated methylenecyclopropanes 1, systems whose photoinduced electron-transfer (PET) chemistry has been thoroughly studied, are described. In both the TL and EL experiments with 1, electronically excited triplet trimethylenemethane (TMM) biradicals 3 2 •• are generated by back electron transfer (charge recombination) of a TMM radical cation (hole) 2 •+, formed by isomerization of the substrate radical cation (hole, 1 •+). The application of this chemistry to the design of new organic light-emitting diodes (OLEDs) is described. The mechanistic features of this reaction system have the potential of overcoming significant problems (e.g., quantum efficiency, difficulty obtaining long wavelength emission, and device durability) normally associated with OLEDs that rely on the use of organic closed-shell hydrocarbons.
AbstractList The results of an investigation of the thermoluminescence (TL) and electroluminescence (EL) of arylated methylenecyclopropanes 1, systems whose photoinduced electron-transfer (PET) chemistry has been thoroughly studied, are described. In both the TL and EL experiments with 1, electronically excited triplet trimethylenemethane (TMM) biradicals 3 2 •• are generated by back electron transfer (charge recombination) of a TMM radical cation (hole) 2 •+, formed by isomerization of the substrate radical cation (hole, 1 •+). The application of this chemistry to the design of new organic light-emitting diodes (OLEDs) is described. The mechanistic features of this reaction system have the potential of overcoming significant problems (e.g., quantum efficiency, difficulty obtaining long wavelength emission, and device durability) normally associated with OLEDs that rely on the use of organic closed-shell hydrocarbons.
The results of an investigation of the thermoluminescence (TL) and electroluminescence (EL) of arylated methylenecyclopropanes 1, systems whose photoinduced electron-transfer (PET) chemistry has been thoroughly studied, are described. In both the TL and EL experiments with 1, electronically excited triplet trimethylenemethane (TMM) biradicals (3)2(center dot center dot) are generated by back electron transfer (charge recombination) of a TMM radical cation (hole) 2(center dot+), formed by isomerization of the substrate radical cation (hole, 1(center dot+)). The application of this chemistry to the design of new organic light-emitting diodes (OLEDs) is described. The mechanistic features of this reaction system have the potential of overcoming significant problems (e.g., quantum efficiency, difficulty obtaining long wavelength emission, and device durability) normally associated with OLEDs that rely on the use of organic closed-shell hydrocarbons.
Author Ikeda, Hiroshi
Mizuno, Kazuhiko
Namai, Hayato
Kato, Nobuyuki
Hoshi, Yosuke
Morishita, Yoshii
Author_xml – sequence: 1
  givenname: Hayato
  surname: Namai
  fullname: Namai, Hayato
– sequence: 2
  givenname: Hiroshi
  surname: Ikeda
  fullname: Ikeda, Hiroshi
– sequence: 3
  givenname: Yosuke
  surname: Hoshi
  fullname: Hoshi, Yosuke
– sequence: 4
  givenname: Nobuyuki
  surname: Kato
  fullname: Kato, Nobuyuki
– sequence: 5
  givenname: Yoshii
  surname: Morishita
  fullname: Morishita, Yoshii
– sequence: 6
  givenname: Kazuhiko
  surname: Mizuno
  fullname: Mizuno, Kazuhiko
BackLink https://www.ncbi.nlm.nih.gov/pubmed/17608421$$D View this record in MEDLINE/PubMed
BookMark eNqNkcFuEzEQhi1URNPCgRdAPiDUqlqwvbvezRHShCKlBNSFAxfL651NnO7awfaq7RtwhjfkSXCUtBy4cPJY-uafmf8_QgfGGkDoOSWvKWH0zVqSgowzfvYIjWjOSJJTxg_QiBDCkqLk6SE68n4dvxkr6RN0SAtOyozREfpVrcD1tht6bcArMAqwNA2W-CPc4IVbSqMVnuvlKiTTXoegzRKfa9sAPlnMp-en-J300GBrcOX0poPw-8fPfYVn3WDdvaptcVjBluohrO46MLAtpIlK1eVlFNJONlrJ7il63MrOw7P9e4y-zKbV5CKZL95_mLydJzKjWUiAFSqvx6niBac0Y4pA2rYSilqNG16meS0Jb6UsGMtLmadSkbRVNeOS1y3kTXqMXu10N85-H8AH0eu4bNfFnezgRRFdzXNSRvBkBypnvXfQik28Qro7QYnYJiDuE4joi73mUPfQ_AX3jkeg3AE3UNvWK7015wHbJpaVtIxjCUnZRAcZtDUTO5gQW8_-vzXSyY7WPsDtAybdteBFWuSi-nQlZunnr1ffJheiivzLHS-VF2s7OBO9__fAP85Dv9U
CitedBy_id crossref_primary_10_1088_1674_0068_25_01_25_30
crossref_primary_10_1007_s11164_012_0658_y
crossref_primary_10_2494_photopolymer_21_327
crossref_primary_10_1021_cr400056a
crossref_primary_10_1039_C7CC08568K
crossref_primary_10_1021_cr400686j
crossref_primary_10_1039_C6RA16580J
crossref_primary_10_1021_jacs_7b12592
crossref_primary_10_1021_ma1020159
crossref_primary_10_1021_jacs_3c07477
crossref_primary_10_1039_c0cp02713h
crossref_primary_10_1021_acs_jpclett_1c00759
crossref_primary_10_1002_ange_200702512
crossref_primary_10_1021_ja074000b
crossref_primary_10_1134_S1070363219120399
crossref_primary_10_1039_c3nj00703k
crossref_primary_10_1039_C7SC04034B
crossref_primary_10_1246_cl_210201
crossref_primary_10_1039_C6CC07898B
crossref_primary_10_1038_s41377_023_01314_z
crossref_primary_10_1039_C4CC06847E
crossref_primary_10_1016_j_mser_2020_100581
crossref_primary_10_1071_CH10167
crossref_primary_10_1021_ja500340f
crossref_primary_10_1039_D2CC04481A
crossref_primary_10_1080_00397911_2012_659830
crossref_primary_10_1088_1361_6463_ad2a12
crossref_primary_10_1007_s11164_018_3282_7
crossref_primary_10_5059_yukigoseikyokaishi_81_501
crossref_primary_10_1039_D2TC03132A
crossref_primary_10_1002_anie_200702512
crossref_primary_10_1007_s00214_009_0694_x
crossref_primary_10_1021_acs_joc_6b00117
crossref_primary_10_1021_acs_inorgchem_6b02864
crossref_primary_10_1039_D0SC04847J
crossref_primary_10_1016_j_dyepig_2013_05_022
crossref_primary_10_1039_D1SC04486A
crossref_primary_10_1039_C2SC21503A
crossref_primary_10_1246_cl_180043
crossref_primary_10_1039_D1TC05268C
crossref_primary_10_1016_j_polymer_2018_03_029
crossref_primary_10_1021_acs_chemrev_3c00613
crossref_primary_10_1021_nn100357m
crossref_primary_10_1016_j_jphotochemrev_2008_11_002
crossref_primary_10_1039_c3cp50581b
crossref_primary_10_1016_j_dyepig_2010_07_010
crossref_primary_10_1039_C5RA14268G
crossref_primary_10_1021_acs_jctc_1c00859
crossref_primary_10_1007_s11426_020_9778_9
crossref_primary_10_1016_j_tet_2011_06_052
crossref_primary_10_1007_s40242_023_2365_1
crossref_primary_10_1021_jp509399x
crossref_primary_10_1021_acsaom_4c00101
crossref_primary_10_3184_174751911X13170609435069
crossref_primary_10_5059_yukigoseikyokaishi_70_434
Cites_doi 10.1021/jo047893o
10.1117/12.567679
10.1038/nature04645
10.1016/j.tetlet.2005.12.063
10.1021/ja0277982
10.1021/jp026902z
10.1016/j.tetlet.2006.01.024
10.1021/ja00209a022
10.1021/ar50142a003
10.1021/ar960002h
10.1039/tf9696502159
10.1021/j100258a017
10.1021/ja00174a028
10.1021/ja00492a037
10.1163/156856793X00370
10.1146/annurev.pc.15.100164.001103
10.1021/ja00287a016
10.1016/0022-2313(71)90068-8
10.1021/cr950017d
10.1021/ja00290a065
10.1007/978-0-387-21720-8_1
ContentType Journal Article
Copyright Copyright © 2007 American Chemical Society
Copyright_xml – notice: Copyright © 2007 American Chemical Society
DBID BSCLL
1KM
BLEPL
DTL
GAMXJ
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
DOI 10.1021/ja070946+
DatabaseName Istex
Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2007
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
MEDLINE - Academic
DatabaseTitle Web of Science
MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
MEDLINE - Academic
DatabaseTitleList
MEDLINE
Web of Science
MEDLINE - Academic
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 2
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1520-5126
EndPage 9036
ExternalDocumentID 10_1021_ja070946
17608421
000248185500032
ark_67375_TPS_F3QVSZCH_T
a813162780
Genre Research Support, Non-U.S. Gov't
Journal Article
GroupedDBID -
.K2
02
186
4.4
53G
55A
5GY
5RE
5VS
7~N
85S
AABXI
ABFLS
ABMVS
ABPPZ
ABPTK
ABUCX
ABUFD
ACGFS
ACJ
ACNCT
ACS
AEESW
AENEX
AETEA
AFEFF
AFFNX
AFMIJ
AIDAL
ALMA_UNASSIGNED_HOLDINGS
ANTXH
AQSVZ
BAANH
BKOMP
CS3
DU5
DZ
EBS
ED
ED~
EJD
ET
F20
F5P
GNL
IH9
IHE
JG
JG~
K2
K78
LG6
OHT
P2P
ROL
RXW
TAE
TAF
TN5
UHB
UI2
UKR
UNC
UPT
UQL
VF5
VG9
VQA
W1F
WH7
X
XFK
YZZ
ZCG
ZE2
ZHY
---
-DZ
-ET
-~X
.DC
6TJ
AAHBH
AAYOK
ABJNI
ABQRX
ACBEA
ACGFO
ADHLV
ADOJD
AGXLV
AHGAQ
BSCLL
CUPRZ
GGK
IH2
XSW
YQT
ZCA
~02
1KM
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
ID FETCH-LOGICAL-a414t-e27c5b93c6761142c0e3ffae7bc9d6835ba06faa72258a53ac03fcb26a6bfe5d3
IEDL.DBID ACS
ISICitedReferencesCount 74
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000248185500032
ISSN 0002-7863
IngestDate Fri Oct 25 09:00:39 EDT 2024
Thu Sep 26 17:22:37 EDT 2024
Sat Sep 28 07:43:08 EDT 2024
Fri Nov 08 20:05:28 EST 2024
Wed Sep 18 07:16:12 EDT 2024
Wed Oct 30 09:27:18 EDT 2024
Thu Aug 27 13:42:09 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 29
Keywords OXIDATION
RECOMBINATION
ARYLMETHYL RADICALS
ELECTRON-TRANSFER
GROUND-STATE
PHOTOCHEMISTRY
RADICAL-ION PAIRS
POTENTIALS
CYCLIZATION
SINGLET
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a414t-e27c5b93c6761142c0e3ffae7bc9d6835ba06faa72258a53ac03fcb26a6bfe5d3
Notes ark:/67375/TPS-F3QVSZCH-T
istex:6FBA6ECCA6A231C46B6058AEE1960870A03B0CE7
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 17608421
PQID 70705508
PQPubID 23479
PageCount 5
ParticipantIDs acs_journals_10_1021_ja070946
webofscience_primary_000248185500032
istex_primary_ark_67375_TPS_F3QVSZCH_T
webofscience_primary_000248185500032CitationCount
proquest_miscellaneous_70705508
crossref_primary_10_1021_ja070946
pubmed_primary_17608421
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
7~N
ACJ
VG9
W1F
ANTXH
ACS
AEESW
AFEFF
.K2
ABMVS
ABUCX
IH9
BAANH
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 2007-07-25
PublicationDateYYYYMMDD 2007-07-25
PublicationDate_xml – month: 07
  year: 2007
  text: 2007-07-25
  day: 25
PublicationDecade 2000
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
– name: United States
PublicationTitle Journal of the American Chemical Society
PublicationTitleAbbrev J AM CHEM SOC
PublicationTitleAlternate J. Am. Chem. Soc
PublicationYear 2007
Publisher American Chemical Society
Amer Chemical Soc
Publisher_xml – name: American Chemical Society
– name: Amer Chemical Soc
References BROMBERG, A (WOS:A1985TZ67700016) 1985; 107
Miyashi, T (WOS:000082827100010) 1999; 32
Ikeda, H (WOS:000235647300039) 2006; 47
SHINAR J (WOS:000248185500032.29) 2004
MARCUS, RA (WOS:A19644987A00014) 1964; 15
SIM, BA (WOS:A1990DW57100027) 1990; 112
Roth, HD (WOS:000182732800035) 2003; 107
Karki, SB (WOS:A1997WC77200022) 1997; 119
MIYASHI, T (WOS:A1985ACC4700065) 1985; 107
COSIMBESCU L (WOS:000248185500032.6) 2005
BARD AJ (WOS:000248185500032.2) 2004
Ikeda, H (WOS:000184364500048) 2003; 125
BROMBERG, A (WOS:A1985AKP8100017) 1985; 89
WORKENTIN, MS (WOS:A1993MM17300006) 1993; 19
BROCKLEHURST, B (WOS:A1969E243600027) 1969; 65
SHINAR J (WOS:000248185500032.28) 2004
SCHUSTER, GB (WOS:A1979HQ19100003) 1979; 12
Deniau, C. (INSPEC:259809) 1971; 3
Allan, AK (WOS:000072490200002) 1998; 1998
Little, RD (WOS:A1996TT87100005) 1996; 96
KALINOWSKI J (WOS:000248185500032.15) 2005
Ikeda, H (WOS:000074301600037) 1998; 120
ROTH HD (WOS:000248185500032.26) 2001; 2
Mak, CSK (WOS:000225811100003) 2004; 5519
Sun, YR (WOS:000236736700035) 2006; 440
Ikeda, H (WOS:000071510300013) 1998; 120
Ikeda, H (WOS:000228983300005) 2005; 70
Roth, HD (WOS:000230007100013) 2005; 77
WAYNER, DDM (WOS:A1988L760000021) 1988; 110
Ikeda, H (WOS:000235415600001) 2006; 47
TURRO, NJ (WOS:A1978FX16500036) 1978; 100
IKEDA, H (WOS:A1994MX13100029) 1994
MULLEN K (WOS:000248185500032.23) 2006
Miyashi, T (CCC:000079869700001) 1999; 6
Electrogenerated Chemiluminescence (ja0709461b00003/ja0709461b00003_1) 2004
Ikeda H. (ja0709461b00009/ja0709461b00009_2) 1994; 297
Miyashi T. (ja0709461b00010/ja0709461b00010_4) 1999; 6
Wayner D. D. M. (ja0709461b00023/ja0709461b00023_1) 1988; 110
For (ja0709461b00007/ja0709461b00007_1) 2006; 440
Little R. D. (ja0709461b00027/ja0709461b00027_1) 1996; 96
Roth H. D. (ja0709461b00008/ja0709461b00008_2) 2005; 77
Ikeda H. (ja0709461b00010/ja0709461b00010_2) 1998; 120
Allan A. K. (ja0709461b00027/ja0709461b00027_2) 1998; 1
Cosimbescu L. (ja0709461b00029/ja0709461b00029_1) 2005
Ikeda H. (ja0709461b00009/ja0709461b00009_1) 1998; 120
Ikeda H. (ja0709461b00010/ja0709461b00010_1) 2003; 125
Miyashi T. (ja0709461b00010/ja0709461b00010_3) 1985; 107
Miyashi T. (ja0709461b00009/ja0709461b00009_3) 1999; 32
Organic Light Emitting-Devices (ja0709461b00006/ja0709461b00006_1) 2006
Roth H. D. (ja0709461b00008/ja0709461b00008_1) 2003; 107
Karki S. B. (ja0709461b00018/ja0709461b00018_1) 1997; 119
Schuster G. B. (ja0709461b00002/ja0709461b00002_1) 1979; 12
Turro N. J. (ja0709461b00015/ja0709461b00015_1) 1978; 100
Bromberg A. (ja0709461b00020/ja0709461b00020_2) 1985; 107
Ikeda H. (ja0709461b00013/ja0709461b00013_1) 2006; 47
Ikeda H. (ja0709461b00016/ja0709461b00016_1) 2005; 70
Deniau C. (ja0709461b00011/ja0709461b00011_1) 1971; 3
Brocklehurst B. (ja0709461b00012/ja0709461b00012_1) 1969; 65
Workentin M. S. (ja0709461b00025/ja0709461b00025_1) 1993; 19
Bromberg A. (ja0709461b00020/ja0709461b00020_1) 1985; 89
ja0709461b00004/ja0709461b00004_2
Organic Light (ja0709461b00005/ja0709461b00005_1) 2005
Organic Light (ja0709461b00004/ja0709461b00004_1) 2004
Roth H. D. (ja0709461b00008/ja0709461b00008_3) 2001; 2
Ikeda H. (ja0709461b00014/ja0709461b00014_1) 2006; 47
Sim B. A. (ja0709461b00024/ja0709461b00024_1) 1990; 112
Marcus R. A. (ja0709461b00001/ja0709461b00001_1) 1964; 15
References_xml – volume: 3
  start-page: 325
  year: 1971
  ident: INSPEC:259809
  article-title: Deferred luminescence spectra of some aromatic compounds in rigid organic media
  publication-title: Journal of Luminescence
  contributor:
    fullname: Deniau, C.
– year: 2004
  ident: WOS:000248185500032.28
  publication-title: ORGANIC LIGHT EMITTI
  contributor:
    fullname: SHINAR J
– volume: 120
  start-page: 87
  year: 1998
  ident: WOS:000071510300013
  article-title: Photoinduced electron-transfer degenerate cope rearrangement of 2,5-diaryl-1,5-hexadienes: A cation-radical cyclization-diradical cleavage mechanism
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: Ikeda, H
– volume: 70
  start-page: 3806
  year: 2005
  ident: WOS:000228983300005
  article-title: An evolved explanation for the molecular geometry and electronic structure of diphenyl-substituted cyclic trimethylenemethane in the ground state: A nearly planar conformation with a considerably localized electronic state
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo047893o
  contributor:
    fullname: Ikeda, H
– year: 2006
  ident: WOS:000248185500032.23
  publication-title: ORGANIC LIGHT EMITTI
  contributor:
    fullname: MULLEN K
– volume: 32
  start-page: 815
  year: 1999
  ident: WOS:000082827100010
  article-title: Photoinduced electron-transfer intramolecular cyclization of acyclic dienes with two styrene units
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  contributor:
    fullname: Miyashi, T
– volume: 1998
  start-page: 1
  year: 1998
  ident: WOS:000072490200002
  article-title: The versatile trimethylenemethane diyl; Diyl trapping reactions - Retrospective and new modes of reactivity
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: Allan, AK
– volume: 5519
  start-page: 24
  year: 2004
  ident: WOS:000225811100003
  article-title: Singlet and triplet emission from polymers for OLED applications
  publication-title: ORGANIC LIGHT-EMITTING MATERIALS AND DEVICES VIII
  doi: 10.1117/12.567679
  contributor:
    fullname: Mak, CSK
– volume: 120
  start-page: 5832
  year: 1998
  ident: WOS:000074301600037
  article-title: Direct observation of two different types of TMM intermediates in the photoinduced electron-transfer degenerate methylenecyclopropane rearrangement
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: Ikeda, H
– volume: 440
  start-page: 908
  year: 2006
  ident: WOS:000236736700035
  article-title: Management of singlet and triplet excitons for efficient white organic light-emitting devices
  publication-title: NATURE
  doi: 10.1038/nature04645
  contributor:
    fullname: Sun, YR
– volume: 47
  start-page: 1857
  year: 2006
  ident: WOS:000235647300039
  article-title: Matrix isolation and DFT calculations of the TMM radical cation generated via the single electron oxidation of a methylenecyclopropane
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2005.12.063
  contributor:
    fullname: Ikeda, H
– volume: 77
  start-page: 1075
  year: 2005
  ident: WOS:000230007100013
  article-title: Return electron transfer in radical ion pairs of triplet multiplicity
  publication-title: PURE AND APPLIED CHEMISTRY
  contributor:
    fullname: Roth, HD
– volume: 65
  start-page: 2159
  year: 1969
  ident: WOS:A1969E243600027
  article-title: ION RECOMBINATION IN GAMMA-IRRADIATED NAPHTHALENE SOLUTIONS
  publication-title: TRANSACTIONS OF THE FARADAY SOCIETY
  contributor:
    fullname: BROCKLEHURST, B
– volume: 112
  start-page: 6635
  year: 1990
  ident: WOS:A1990DW57100027
  article-title: THERMODYNAMIC SIGNIFICANCE OF RHO+ AND RHO- FROM SUBSTITUENT EFFECTS ON THE REDOX POTENTIALS OF ARYLMETHYL RADICALS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: SIM, BA
– start-page: 1
  year: 2004
  ident: WOS:000248185500032.29
  publication-title: ORGANIC LIGHT EMITTI
  contributor:
    fullname: SHINAR J
– volume: 12
  start-page: 366
  year: 1979
  ident: WOS:A1979HQ19100003
  article-title: CHEMI-LUMINESCENCE OF ORGANIC PEROXIDES - CONVERSION OF GROUND-STATE REACTANTS TO EXCITED-STATE PRODUCTS BY THE CHEMICALLY-INITIATED ELECTRON-EXCHANGE LUMINESCENCE MECHANISM
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  contributor:
    fullname: SCHUSTER, GB
– volume: 89
  start-page: 2507
  year: 1985
  ident: WOS:A1985AKP8100017
  article-title: PHOTOPHYSICS OF ARYLMETHYL RADICALS AT 77-K - STRUCTURE PHOTOREACTIVITY CORRELATION
  publication-title: JOURNAL OF PHYSICAL CHEMISTRY
  contributor:
    fullname: BROMBERG, A
– start-page: 297
  year: 1994
  ident: WOS:A1994MX13100029
  article-title: STRIKING CONTRAST BETWEEN PHOTOINDUCED AND NON-PHOTOINDUCED ELECTRON-TRANSFER REACTIONS OF 1,4-DIPHENYL-2,3-DIAZABICYCLO[2.2.2]OCT-2-ENE
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
  contributor:
    fullname: IKEDA, H
– volume: 125
  start-page: 9147
  year: 2003
  ident: WOS:000184364500048
  article-title: Spectroscopic and calorimetric studies on the mechanism of methylenecyclopropane rearrangements triggered by photoinduced electron transfer
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja0277982
  contributor:
    fullname: Ikeda, H
– volume: 119
  start-page: 431
  year: 1997
  ident: WOS:A1997WC77200022
  article-title: Bond-coupled electron transfer processes: A new strategy for high-efficiency photoinduced electron transfer reactions
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: Karki, SB
– year: 2005
  ident: WOS:000248185500032.15
  publication-title: ORGANIC LIGHT EMITTI
  contributor:
    fullname: KALINOWSKI J
– volume: 100
  start-page: 7653
  year: 1978
  ident: WOS:A1978FX16500036
  article-title: EVIDENCE FROM ABSORPTION AND EMISSION-SPECTRA OF TRIMETHYLENEMETHANE DERIVATIVES FOR 2 MOLECULAR-SPECIES IN THERMAL-EQUILIBRIUM
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: TURRO, NJ
– volume: 19
  start-page: 777
  year: 1993
  ident: WOS:A1993MM17300006
  article-title: ORGANIC BASED REDUCING AGENTS - PREDICTION OF OXIDATION POTENTIALS OF ELECTRON-RICH RADICALS FROM THE ANALYSIS OF AM1 CHARGE-DENSITY DISTRIBUTIONS
  publication-title: RESEARCH ON CHEMICAL INTERMEDIATES
  contributor:
    fullname: WORKENTIN, MS
– volume: 6
  start-page: 1
  year: 1999
  ident: CCC:000079869700001
  article-title: Photoinduced electron transfer reactions of cyclopropane derivatives
  publication-title: ADVANCES IN ELECTRON TRANSFER CHEMISTRY, VOL 6, 1999
  contributor:
    fullname: Miyashi, T
– volume: 2
  start-page: 93
  year: 2001
  ident: WOS:000248185500032.26
  publication-title: J PHOTOCH PHOTOBIO C
  contributor:
    fullname: ROTH HD
– volume: 110
  start-page: 132
  year: 1988
  ident: WOS:A1988L760000021
  article-title: OXIDATION AND REDUCTION POTENTIALS OF TRANSIENT FREE-RADICALS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: WAYNER, DDM
– volume: 107
  start-page: 3432
  year: 2003
  ident: WOS:000182732800035
  article-title: Electron-transfer photochemistry of cis- and trans-1,2-diphenylcyclopropane with singlet acceptors: Recombination of radical ion pairs of singlet and triplet multiplicity
  publication-title: JOURNAL OF PHYSICAL CHEMISTRY A
  doi: 10.1021/jp026902z
  contributor:
    fullname: Roth, HD
– volume: 47
  start-page: 1501
  year: 2006
  ident: WOS:000235415600001
  article-title: The first observation in an organic medium and DFT calculation of the TMM radical anion generated via a single electron reduction of a methylenecyclopropane
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2006.01.024
  contributor:
    fullname: Ikeda, H
– year: 2005
  ident: WOS:000248185500032.6
  publication-title: US PAT APPL PUBL
  contributor:
    fullname: COSIMBESCU L
– volume: 107
  start-page: 83
  year: 1985
  ident: WOS:A1985TZ67700016
  article-title: PHOTOPHYSICS AND PHOTOCHEMISTRY OF ARYLMETHYL RADICALS IN LIQUIDS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: BROMBERG, A
– volume: 96
  start-page: 93
  year: 1996
  ident: WOS:A1996TT87100005
  article-title: Diyl trapping and electroreductive cyclization reactions
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: Little, RD
– year: 2004
  ident: WOS:000248185500032.2
  publication-title: ELECTROGENERATED CHE
  contributor:
    fullname: BARD AJ
– volume: 107
  start-page: 1079
  year: 1985
  ident: WOS:A1985ACC4700065
  article-title: EVIDENCE FOR 2 DIFFERENT RADICAL CATION TYPES DERIVED FROM METHYLENECYCLOPROPANE
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: MIYASHI, T
– volume: 15
  start-page: 155
  year: 1964
  ident: WOS:A19644987A00014
  article-title: CHEMICAL + ELECTROCHEMICAL ELECTRON-TRANSFER THEORY
  publication-title: ANNUAL REVIEW OF PHYSICAL CHEMISTRY
  contributor:
    fullname: MARCUS, RA
– volume: 110
  start-page: 137
  year: 1988
  ident: ja0709461b00023/ja0709461b00023_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00209a022
  contributor:
    fullname: Wayner D. D. M.
– volume: 12
  start-page: 373
  year: 1979
  ident: ja0709461b00002/ja0709461b00002_1
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar50142a003
  contributor:
    fullname: Schuster G. B.
– volume: 119
  start-page: 432
  year: 1997
  ident: ja0709461b00018/ja0709461b00018_1
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Karki S. B.
– volume: 120
  start-page: 95
  year: 1998
  ident: ja0709461b00009/ja0709461b00009_1
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Ikeda H.
– volume: 440
  start-page: 912
  year: 2006
  ident: ja0709461b00007/ja0709461b00007_1
  publication-title: Nature
  contributor:
    fullname: For
– volume: 32
  start-page: 824
  year: 1999
  ident: ja0709461b00009/ja0709461b00009_3
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar960002h
  contributor:
    fullname: Miyashi T.
– volume-title: Springer-Verlag:  New York
  year: 2004
  ident: ja0709461b00004/ja0709461b00004_1
  contributor:
    fullname: Organic Light
– volume: 297
  start-page: 298
  year: 1994
  ident: ja0709461b00009/ja0709461b00009_2
  publication-title: J. Chem. Soc., Chem. Commun.
  contributor:
    fullname: Ikeda H.
– volume: 6
  start-page: 39
  year: 1999
  ident: ja0709461b00010/ja0709461b00010_4
  publication-title: London
  contributor:
    fullname: Miyashi T.
– volume: 65
  start-page: 2167
  year: 1969
  ident: ja0709461b00012/ja0709461b00012_1
  publication-title: Trans. Faraday. Soc.
  doi: 10.1039/tf9696502159
  contributor:
    fullname: Brocklehurst B.
– volume: 89
  start-page: 2513
  year: 1985
  ident: ja0709461b00020/ja0709461b00020_1
  publication-title: J. Phys. Chem.
  doi: 10.1021/j100258a017
  contributor:
    fullname: Bromberg A.
– volume: 2
  start-page: 116
  year: 2001
  ident: ja0709461b00008/ja0709461b00008_3
  publication-title: J. Photochem. Photobiol. C.
  contributor:
    fullname: Roth H. D.
– volume-title: 25
  year: 2005
  ident: ja0709461b00029/ja0709461b00029_1
  contributor:
    fullname: Cosimbescu L.
– volume: 125
  start-page: 9157
  year: 2003
  ident: ja0709461b00010/ja0709461b00010_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja0277982
  contributor:
    fullname: Ikeda H.
– volume: 112
  start-page: 6638
  year: 1990
  ident: ja0709461b00024/ja0709461b00024_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00174a028
  contributor:
    fullname: Sim B. A.
– volume: 100
  start-page: 7658
  year: 1978
  ident: ja0709461b00015/ja0709461b00015_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00492a037
  contributor:
    fullname: Turro N. J.
– volume: 19
  start-page: 785
  year: 1993
  ident: ja0709461b00025/ja0709461b00025_1
  publication-title: Res. Chem. Intermed.
  doi: 10.1163/156856793X00370
  contributor:
    fullname: Workentin M. S.
– volume: 120
  start-page: 5833
  year: 1998
  ident: ja0709461b00010/ja0709461b00010_2
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Ikeda H.
– volume: 77
  start-page: 1085
  year: 2005
  ident: ja0709461b00008/ja0709461b00008_2
  publication-title: Pure Appl. Chem.
  contributor:
    fullname: Roth H. D.
– volume-title: Principles, Characteristics, and Processes
  year: 2005
  ident: ja0709461b00005/ja0709461b00005_1
  contributor:
    fullname: Organic Light
– volume: 107
  start-page: 3437
  year: 2003
  ident: ja0709461b00008/ja0709461b00008_1
  publication-title: J. Phys. Chem. A.
  contributor:
    fullname: Roth H. D.
– volume: 47
  start-page: 1860
  year: 2006
  ident: ja0709461b00013/ja0709461b00013_1
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Ikeda H.
– volume: 70
  start-page: 3813
  year: 2005
  ident: ja0709461b00016/ja0709461b00016_1
  publication-title: J. Org. Chem.
  contributor:
    fullname: Ikeda H.
– volume-title: Marcel Dekker:  New York
  year: 2004
  ident: ja0709461b00003/ja0709461b00003_1
  contributor:
    fullname: Electrogenerated Chemiluminescence
– volume: 15
  start-page: 196
  year: 1964
  ident: ja0709461b00001/ja0709461b00001_1
  publication-title: Ann. Rev. Phys. Chem.
  doi: 10.1146/annurev.pc.15.100164.001103
  contributor:
    fullname: Marcus R. A.
– volume: 107
  start-page: 91
  year: 1985
  ident: ja0709461b00020/ja0709461b00020_2
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00287a016
  contributor:
    fullname: Bromberg A.
– volume: 3
  start-page: 350
  year: 1971
  ident: ja0709461b00011/ja0709461b00011_1
  publication-title: J. Lumin.
  doi: 10.1016/0022-2313(71)90068-8
  contributor:
    fullname: Deniau C.
– volume-title: Properties and Applications
  year: 2006
  ident: ja0709461b00006/ja0709461b00006_1
  contributor:
    fullname: Organic Light Emitting-Devices
– volume: 96
  start-page: 114
  year: 1996
  ident: ja0709461b00027/ja0709461b00027_1
  publication-title: Chem. Rev.
  doi: 10.1021/cr950017d
  contributor:
    fullname: Little R. D.
– volume: 47
  start-page: 1504
  year: 2006
  ident: ja0709461b00014/ja0709461b00014_1
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Ikeda H.
– volume: 107
  start-page: 1080
  year: 1985
  ident: ja0709461b00010/ja0709461b00010_3
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja00290a065
  contributor:
    fullname: Miyashi T.
– volume: 1
  start-page: 12
  year: 1998
  ident: ja0709461b00027/ja0709461b00027_2
  publication-title: Eur. J. Org. Chem.
  contributor:
    fullname: Allan A. K.
– ident: ja0709461b00004/ja0709461b00004_2
  doi: 10.1007/978-0-387-21720-8_1
SSID ssj0004281
Score 2.2269783
Snippet The results of an investigation of the thermoluminescence (TL) and electroluminescence (EL) of arylated methylenecyclopropanes 1, systems whose photoinduced...
Source Web of Science
SourceID proquest
crossref
pubmed
webofscience
istex
acs
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 9032
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Free Radicals - chemistry
Gamma Rays
Indicators and Reagents
Luminescence
Magnetic Resonance Spectroscopy
Physical Sciences
Science & Technology
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Title Thermoluminescence and a New Organic Light-Emitting Diode (OLED) Based on Triplet−Triplet Fluorescence of the Trimethylenemethane (TMM) Biradical
URI http://dx.doi.org/10.1021/ja070946
https://api.istex.fr/ark:/67375/TPS-F3QVSZCH-T/fulltext.pdf
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000248185500032
https://www.ncbi.nlm.nih.gov/pubmed/17608421
https://search.proquest.com/docview/70705508
Volume 129
WOS 000248185500032
WOSCitedRecordID wos000248185500032
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwEB6V9gAX3o8ABYMqBEKpHDuxs0dId7VCXR7aFFW9RLbjSKvSBGWzEvALOMM_5JcwzqMtYnncLMVxkpnxzDgz8w3AjuuobaXhvmQ5HlB0JHwdFzhSiucWTWDUwjXNXovpQfjqMDrcgMd_iOAzhw-EUjkKxQXYYhL3hHN_kvlZ7SOLg8HFlbHgA3rQuTufO8tjlr9Yni1HxE_r3Mq1Fqi1NpMrkAw1O12SyfHuqtG75svvEI5_-ZCrcLl3NsmLTjquwYYtr8PFZOjxdgO-o5TUJ05Buex3496EqDIniqDyI12dpiH7LdjI-GTR5kiTvUWVW_L0zf547xl5iVYwJ1VJ0tr9sm9-fP3Wj8jkw6qqh1WrgqCr6Wa5ntWf0dZZN1AlrpTOZrjQolZtzOgmHEzGaTL1-zYNvgqDsPEtkybSI26EFK4y11DLi0JZqc0oF-jhaUVFoZRE1RGriCtDeWE0E0rowkY5vwWbZVXaO0BGVKuA60LaIEfXIdIRRf1baE1zYRnnHmwjI7N-my2zNoLO8ATTk9aDRwOLs48dWseaOU9a3p9OUPWxy26TUZa-nWcT_u79_CiZZqkHDwfhyJAtLpCCRKlWy0xSh0FEYw9udzJz9jApaByywIOd80J0ep22GHKBQ5FDdco8CP5nWtLDtTuYgubuP2hwDy4N_59ZdB82m3plt9FxavSDduf8BCQ3ESs
link.rule.ids 315,783,787,2772,27088,27936,27937,57066,57116
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NbtQwELagPZQL_z8plBqpQiCUyoljO3uE7a4W2C2gTVHVS2Q7jrQqTaokKwFPwBnekCdh7CTdglaiN0txHGc8nhl7Zr5BaM9W1DZCU1-EGRxQFOO-inNoSUkzAyqQObim2SGfHEXvjtlxB5Njc2FgEjWMVDsn_gpdwMIEAXMOIv7qOtpkAhSlNYOG81UOZBgHvakrYk57FKHLr1oNpOu_NNCmJebXdeblWk3ktM74Vlu-yM3XBZuc7i8bta-__wPleLUfuo1udsYnft1yyx10zRR30dawr_l2D_0CrqnOrMCy0fDazgjLIsMSgzDEbd6mxlMHPjI6W7iYaXywKDODX3yYjg5e4jegFTNcFjip7BV-8_vHz66Fx1-WZdWPWuYYTE_by9aw_ga6z9iGLGCkZDaDgRaVdD6k--hoPEqGE78r2-DLKIga34RCMzWgmgtuM3U1MTTPpRFKDzIOFp-ShOdSChAlsWRUakJzrUIuucoNy-gDtFGUhXmE8IAoGVCVCxNkYEowxQjI41wpknETUuqhHSBt2m27OnUe9RBONB1tPfSsX-r0vEXvWNPnueOBiw6yOrXRboKlycd5OqafPs9PhpM08dBuzyQpLIt1rABRymWdCmIxiUjsoYct76w-JjiJozDw0N5lZrp4ThymXGBR5UC8hh4KrtJt2MG3W9iCZvs_NNhFW5NkNk2nbw_fP0Y3-rvpkD1BG021NDtgVDXqqdtNfwCN9Rno
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1fb9MwELdgk4AX_v8JMGakCYFQpiSO7fRxpI0KtNtQs2niJbIdR6rGkilJJeAT8AzfkE_C2U26gSqxN0u5OM75fHf2-X6H0I6pqK25Ii4PctigSMpcGRXQEoLkGkwgtXBN0302Pgo_nNCTbqNocmFgEA301NggvlnV53nRIQwYqCAQ0EHI3l5Hm5T7Niy7F88u8iCDyO_dXR4x0iMJXX7VWCHV_GWFNg1Dv65zMddaI2t5kjvoYDVme-HkdHfRyl31_R84x6v_1F10u3NC8d5Sau6ha7q8j27Gfe23B-gXSE99ZhSXuRWvzKiwKHMsMChFvMzfVHhiQUhGZ3N7dxoP51Wu8euDyWj4Br8D65jjqsRpbY7y298_fnYtnHxZVHXfa1VgcEENlall_Q1soDYNUUJP6XQKHc1rYWNJD9FRMkrjsduVb3BF6IetqwOuqBwQxTgzGbvK06QohOZSDXIGnp8UHiuE4KBSIkGJUB4plAyYYLLQNCeP0EZZlfoJwgNPCp_Igms_B5eCSuqBXi6k9HKmA0IctAXszbrl12Q2sh7AzqbjrYNe9tOdnS9RPNbQvLJysCIQ9am59cZplh7OsoR8Op59jsdZ6qDtXlAymBYTYAGmVIsm457BJvIiBz1eys_FxzjzojDwHbRzWaBWzz2LLecbdDlQs4GD_KuQxR2Mu4EvaJ_-hwfb6MbhMMkm7_c_PkO3-iPqgD5HG2290FvgW7XyhV1QfwCMiBxi
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Thermoluminescence+and+a+New+Organic+Light-Emitting+Diode+%28OLED%29+Based+on+Triplet%E2%88%92Triplet+Fluorescence+of+the+Trimethylenemethane+%28TMM%29+Biradical&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Namai%2C+Hayato&rft.au=Ikeda%2C+Hiroshi&rft.au=Hoshi%2C+Yosuke&rft.au=Kato%2C+Nobuyuki&rft.date=2007-07-25&rft.issn=0002-7863&rft.eissn=1520-5126&rft.volume=129&rft.issue=29&rft.spage=9032&rft.epage=9036&rft_id=info:doi/10.1021%2Fja070946%2B&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_ja070946
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0002-7863&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0002-7863&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0002-7863&client=summon