Design and Synthesis of Novel Calamitic and Discotic Materials Based on the Photorefractive Carbazole Unit

The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known bipheny...

Full description

Saved in:
Bibliographic Details
Published inMolecular Crystals and Liquid Crystals Vol. 518; no. 1; pp. 84 - 100
Main Authors Manickam, M., Iqbal, P., Spencer, N., Ashton, P. R., Kumar, S., Donovan, K. J., Preece, J. A.
Format Journal Article
LanguageEnglish
Published Philadelphia Taylor & Francis Group 01.01.2010
Taylor & Francis Ltd
Subjects
Alkylation
Anisotropic ordering
calamitic liquid crystals
carbazole
Carbazoles
Carboxylic acids
Chemical compounds
Crystals
Derivatives
Differential scanning calorimetry
discotic liquid crystals
Liquid crystal polymers
Liquid crystals
mesogenic
Phase transitions
photorefractive
Photorefractivity
Synthesis
Online AccessGet full text

Cover

Abstract The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known biphenyl and triphenylene liquid-crystalline moieties was synthesized and characterized. These modifications were achieved by the esterification of bishydroxy carbazole derivatives with monoalkylated biphenyl carboxylic acids and alkylation of bisacylated bromo- derivatives of carbazole with monohydroxy pentaalkoxy triphenylene. The pure compounds are not liquid-crystalline, even when doped with trinitrofluorenone (TNF), unlike triphenylene/carbazole materials that we reported previously. These compounds, although not liquid-crystalline, may be of interest in the field of photorefractivity.
AbstractList The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known biphenyl and triphenylene liquidcrystalline moieties was synthesized and characterized. These modifications were achieved by the esterification of bishydroxy carbazole derivatives with monoalkylated biphenyl carboxylic acids and alkylation of bisacylated bromo- derivatives of carbazole with monohydroxy pentaalkoxy triphenylene. The pure compounds are not liquid-crystalline, even when doped with trinitrofluorenone (TNF), unlike triphenylene/carbazole materials that we reported previously. These compounds, although not liquid-crystalline, may be of interest in the field of photorefractivity. [PUBLICATION ABSTRACT]
The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known biphenyl and triphenylene liquid-crystalline moieties was synthesized and characterized. These modifications were achieved by the esterification of bishydroxy carbazole derivatives with monoalkylated biphenyl carboxylic acids and alkylation of bisacylated bromo- derivatives of carbazole with monohydroxy pentaalkoxy triphenylene. The pure compounds are not liquid-crystalline, even when doped with trinitrofluorenone (TNF), unlike triphenylene/carbazole materials that we reported previously. These compounds, although not liquid-crystalline, may be of interest in the field of photorefractivity.
Author Iqbal, P.
Donovan, K. J.
Ashton, P. R.
Preece, J. A.
Manickam, M.
Spencer, N.
Kumar, S.
Author_xml – sequence: 1
  givenname: M.
  surname: Manickam
  fullname: Manickam, M.
  email: m.manickam@bham.ac.uk
  organization: School of Chemistry, The University of Birmingham
– sequence: 2
  givenname: P.
  surname: Iqbal
  fullname: Iqbal, P.
  organization: School of Chemistry, The University of Birmingham
– sequence: 3
  givenname: N.
  surname: Spencer
  fullname: Spencer, N.
  organization: School of Chemistry, The University of Birmingham
– sequence: 4
  givenname: P. R.
  surname: Ashton
  fullname: Ashton, P. R.
  organization: School of Chemistry, The University of Birmingham
– sequence: 5
  givenname: S.
  surname: Kumar
  fullname: Kumar, S.
  organization: Raman Research Institute
– sequence: 6
  givenname: K. J.
  surname: Donovan
  fullname: Donovan, K. J.
  organization: Physics Department , Queen Mary, University of London
– sequence: 7
  givenname: J. A.
  surname: Preece
  fullname: Preece, J. A.
  organization: School of Chemistry, The University of Birmingham
BookMark eNqFkE1PAyEQhompiVb9Ad6IJy-rsCwLm3jR-pn4lahnwrJgabZQgar110utJ030xEzyPMPMOwQD550GYBejA4w4OsS0KnGFUIMIrTmi1RrYxLQmBS05GyzrqiwyUG-AYYwThMqKYb4JJqc62mcHpevgw8KlcW4j9Abe-lfdw5Hs5dQmq76AUxuVXzY3MulgZR_hiYy6g97BbML7sU8-aBOkSvZVZzu08sP3Gj45m7bBusmK3vl-t8DT-dnj6LK4vru4Gh1fF6piZSoIrbRkra5aTZkxtWJdw02NG8M5UiXuWopL3Da0oUZ3vMasw6ztFCMEMSIN2QL7q7mz4F_mOiYxzXvrvpdO-3kUuOSkbhDlTUb3fqATPw8ubyeWMdKaMpQhvIJU8DHm88Qs2KkMC4GRWIYvfoWfnaOVY53xYSrffOg7keSi9yHH45TNP_yls3_1X5ZI74l8AgfNncY
CitedBy_id crossref_primary_10_1016_j_jlumin_2024_120523
crossref_primary_10_1021_acs_chemrev_5b00190
crossref_primary_10_1002_ijch_201200058
crossref_primary_10_1007_s11164_012_0777_5
crossref_primary_10_1039_D1CE01470F
Cites_doi 10.1080/00150190214420
10.1016/j.chemphys.2005.09.036
10.1039/cc9960000559
10.1080/714965597
10.1126/science.288.5474.2181
10.1055/s-1998-2133
10.1103/PhysRevLett.66.1846
10.1063/1.1754607
10.1039/a807158f
10.1080/026782999203760
10.1039/ft9938900037
10.1126/science.278.5345.1924
10.1049/el:19730096
10.1021/cm970127w
10.1364/JOSAB.9.002059
10.1080/026782900202598
10.1016/0038-1098(90)90952-8
10.1002/macp.1987.021880415
10.1039/jm9960601231
10.1021/ma00181a024
10.1103/PhysRevB.46.9900
10.1039/a809313j
10.1038/371497a0
10.1039/a705129h
10.1021/ja952907g
10.1002/adma.19960081010
ContentType Journal Article
Copyright Copyright Taylor & Francis Group, LLC 2010
Copyright Taylor & Francis Ltd. 2010
Copyright_xml – notice: Copyright Taylor & Francis Group, LLC 2010
– notice: Copyright Taylor & Francis Ltd. 2010
DBID AAYXX
CITATION
7SP
7U5
8FD
L7M
DOI 10.1080/15421400903568054
DatabaseName CrossRef
Electronics & Communications Abstracts
Solid State and Superconductivity Abstracts
Technology Research Database
Advanced Technologies Database with Aerospace
DatabaseTitle CrossRef
Solid State and Superconductivity Abstracts
Technology Research Database
Advanced Technologies Database with Aerospace
Electronics & Communications Abstracts
DatabaseTitleList Solid State and Superconductivity Abstracts
Technology Research Database
DeliveryMethod fulltext_linktorsrc
Discipline Engineering
Languages & Literatures
EISSN 1563-5287
1527-1943
EndPage 100
ExternalDocumentID 2047323481
10_1080_15421400903568054
457281
Genre Liquid Crystals
Feature
GroupedDBID .7F
.QJ
0BK
0R~
123
29M
2CH
2F5
30N
4.4
5VS
AAAVI
AAENE
AAJMT
AALDU
AAMIU
AAPUL
AAQRR
ABBKH
ABCCY
ABFIM
ABJVF
ABLIJ
ABPEM
ABPTK
ABQHQ
ABTAI
ABXUL
ACGEJ
ACGFS
ACGOD
ACTIO
ADCVX
ADGTB
ADXPE
AEGYZ
AEISY
AENEX
AEOZL
AEPSL
AEYOC
AFKVX
AFOLD
AFWLO
AGDLA
AGMYJ
AHDLD
AIJEM
AIRXU
AJWEG
AKBVH
AKOOK
ALMA_UNASSIGNED_HOLDINGS
ALQZU
AQRUH
AVBZW
AWYRJ
BLEHA
CAG
CCCUG
CE4
COF
DGEBU
DKSSO
DU5
EBS
EJD
E~A
E~B
FUNRP
FVPDL
GTTXZ
H13
HF~
HZ~
H~P
J.P
KYCEM
M4Z
NA5
NW0
O9-
PQEST
PQQKQ
RIG
RNANH
ROSJB
RTWRZ
S-T
SNACF
TCY
TFL
TFT
TFW
TTHFI
TWF
UT5
UU3
V1K
ZGOLN
~S~
AAYXX
ABPAQ
ABXYU
ABZMO
ADOGB
AHDZW
CITATION
TBQAZ
TDBHL
TUROJ
7SP
7U5
8FD
L7M
ID FETCH-LOGICAL-c472t-354ea7be4be57ff6c7d98f619f880c21db5121b9595fed8617d17bdc733073af3
ISSN 1542-1406
IngestDate Fri Oct 25 22:54:16 EDT 2024
Wed Nov 06 02:48:16 EST 2024
Fri Aug 23 01:11:47 EDT 2024
Tue Jun 13 19:33:42 EDT 2023
Mon May 13 12:09:06 EDT 2019
IsPeerReviewed true
IsScholarly true
Issue 1
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c472t-354ea7be4be57ff6c7d98f619f880c21db5121b9595fed8617d17bdc733073af3
Notes ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
PQID 356856570
PQPubID 53041
PageCount 17
ParticipantIDs proquest_miscellaneous_1283690589
proquest_journals_356856570
informaworld_taylorfrancis_310_1080_15421400903568054
crossref_primary_10_1080_15421400903568054
PublicationCentury 2000
PublicationDate 2010-01-01
PublicationDateYYYYMMDD 2010-01-01
PublicationDate_xml – month: 01
  year: 2010
  text: 2010-01-01
  day: 01
PublicationDecade 2010
PublicationPlace Philadelphia
PublicationPlace_xml – name: Philadelphia
PublicationTitle Molecular Crystals and Liquid Crystals
PublicationYear 2010
Publisher Taylor & Francis Group
Taylor & Francis Ltd
Publisher_xml – name: Taylor & Francis Group
– name: Taylor & Francis Ltd
References CIT0010
Demus D. (CIT0025) 1998
Markovitski D. (CIT0028) 1993; 89
CIT0012
see Lux M. (CIT0013) 1987; 188
CIT0011
Markovitski D. (CIT0018) 1993; 89
Maruyama S. (CIT0026) 1999
Ashkin A. (CIT0003) 1996; 9
CIT0015
CIT0017
CIT0019
Simmerr J. (CIT0016) 1996; 8
CIT0021
CIT0020
CIT0001
CIT0023
CIT0022
Günter P. (CIT0005) 1998
CIT0002
CIT0024
CIT0027
CIT0004
CIT0007
CIT0029
CIT0006
CIT0009
CIT0008
Marcher B. (CIT0014) 1998; 21
References_xml – ident: CIT0021
  doi: 10.1080/00150190214420
– ident: CIT0019
  doi: 10.1016/j.chemphys.2005.09.036
– ident: CIT0007
  doi: 10.1039/cc9960000559
– ident: CIT0020
  doi: 10.1080/714965597
– ident: CIT0024
  doi: 10.1126/science.288.5474.2181
– ident: CIT0029
  doi: 10.1055/s-1998-2133
– ident: CIT0009
  doi: 10.1103/PhysRevLett.66.1846
– volume: 9
  start-page: 72
  year: 1996
  ident: CIT0003
  publication-title: Appl. Phys. Lett.
  doi: 10.1063/1.1754607
  contributor:
    fullname: Ashkin A.
– start-page: 41
  year: 1999
  ident: CIT0026
  publication-title: J. Chem. Soc. Perkin Trans. 1
  doi: 10.1039/a807158f
  contributor:
    fullname: Maruyama S.
– ident: CIT0027
  doi: 10.1080/026782999203760
– volume: 89
  start-page: 37
  year: 1993
  ident: CIT0018
  publication-title: J. Chem. Soc., Faraday Trans.
  doi: 10.1039/ft9938900037
  contributor:
    fullname: Markovitski D.
– ident: CIT0023
  doi: 10.1126/science.278.5345.1924
– ident: CIT0017
  doi: 10.1049/el:19730096
– ident: CIT0011
  doi: 10.1021/cm970127w
– volume-title: Handbook of Liquid Crystal
  year: 1998
  ident: CIT0025
  contributor:
    fullname: Demus D.
– volume: 89
  start-page: 37
  year: 1993
  ident: CIT0028
  publication-title: J. Chem. Soc., Faraday Trans.
  doi: 10.1039/ft9938900037
  contributor:
    fullname: Markovitski D.
– volume-title: Photorefractive Materials and Their Applications
  year: 1998
  ident: CIT0005
  contributor:
    fullname: Günter P.
– ident: CIT0008
  doi: 10.1364/JOSAB.9.002059
– ident: CIT0015
  doi: 10.1080/026782900202598
– ident: CIT0010
  doi: 10.1016/0038-1098(90)90952-8
– volume: 188
  start-page: 811
  year: 1987
  ident: CIT0013
  publication-title: Makromol. Chem.
  doi: 10.1002/macp.1987.021880415
  contributor:
    fullname: see Lux M.
– ident: CIT0022
  doi: 10.1039/jm9960601231
– volume: 21
  start-page: 677
  year: 1998
  ident: CIT0014
  publication-title: Macromolecules
  doi: 10.1021/ma00181a024
  contributor:
    fullname: Marcher B.
– ident: CIT0004
  doi: 10.1103/PhysRevB.46.9900
– ident: CIT0006
  doi: 10.1039/a809313j
– ident: CIT0012
  doi: 10.1038/371497a0
– ident: CIT0002
  doi: 10.1039/a705129h
– ident: CIT0001
  doi: 10.1021/ja952907g
– volume: 8
  start-page: 815
  year: 1996
  ident: CIT0016
  publication-title: Adv. Mater.
  doi: 10.1002/adma.19960081010
  contributor:
    fullname: Simmerr J.
SSID ssj0024718
ssj0000993
Score 1.8981133
Snippet The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over...
SourceID proquest
crossref
informaworld
SourceType Aggregation Database
Enrichment Source
Publisher
StartPage 84
SubjectTerms Alkylation
Anisotropic ordering
calamitic liquid crystals
carbazole
Carbazoles
Carboxylic acids
Chemical compounds
Crystals
Derivatives
Differential scanning calorimetry
discotic liquid crystals
Liquid crystal polymers
Liquid crystals
mesogenic
Phase transitions
photorefractive
Photorefractivity
Synthesis
Title Design and Synthesis of Novel Calamitic and Discotic Materials Based on the Photorefractive Carbazole Unit
URI https://www.tandfonline.com/doi/abs/10.1080/15421400903568054
https://www.proquest.com/docview/356856570
https://search.proquest.com/docview/1283690589
Volume 518
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1bb9MwFLaq7QUeEFdRBshIPFGl5ObYeRwUVCF1qqATEy9VHDtqR0m6Lp3Yfhq_juNL3IygCfZStc7FVs7Xcz6fnAtCrzlQEKHapMqCZR7YW-HxjBLPJ4yGiQChpyobeXKUjI_jTyfkpNf71Ypa2tZ8mF_9Na_kNlKFMZCrypL9D8m6m8IAfAf5widIGD7_ScYjHX5hoi8vS6BytrrIUXUhVyrtKvuxbAqyjpbneaV-TLLarG3wDiyYsG8LBtNFVaumIzpr6kKqSBCeXanYQ0VL2xx20nTUHeSbSyCXK1PmebU82y7Fbgyoq_LWqDKU64UJyZ1mQ-2CUKFqLRfEJCuX-XeDzMnQgfXMNCMYTN3Ql7XSQxuTIeager6wKQDT4eDzsO3G0NFwbTfGrNNRpOV8s6o5Dj3YDtrC2XYsiWArbU221edkp9AdcI12Ns3orJ0PdIXUrgkxMZdqNphMebFIwnwS7-yli2KMCQ1V1v9-CEoOtOv-4Xj07euu0iPV3mW37uadOvPfdu5-jRVdq5nb4Qia-Mzuo3t2x4IPDfweoJ4sH6K7rTqWj9CpASIGGGAHRFwVWAMROyDqExogYgdErIGIqxLDlfgPIGIHRKyA-Bgdf_wwez_2bBMPL49pWHsRiWVGuYy5JLQokpyKlBWwbS_AcuRhIDhQzoCnJCWFFAwItQgoFzmNlPXJiugJ2iurUj5FGO4TMBYzTqMg5lGUSpkLv2C-hF2FZH4fvWke4nxtarXMA1sCt_PE-8hvP-Z5rQFYGOx1T5_XP-s-IjdcEt0w1UEjwrnVHnA6HFMhB7DqV-4oqHb1vi4rZbWFRQD1T1LV9_PZLWc-QHd2_7XnaK_ebOULINE1f2nR-htARcEX
link.rule.ids 315,783,787,27936,27937,60214,61003
linkProvider Library Specific Holdings
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT9wwEB5ROFAOLaWgbpeHkThVCiSbOHaOZQEtlF0hARK3KI5tAUUJYr2o5dd3Jg8KLOLAMfLYcWJ75vN4_A3AlkIIoilNqrEy89Deak9lgns-l6IXaxz0hG4jD0fx4Dw6uuAXjcNt3IRV0h7a1kQRla6mxU3O6DYkbgfNfg83BuRi4LFE0PEB5mIi_6IrHP7oP9eeqPx7JO6hfNyear7WxDO79Iy1dEpLV6bn4DOkbafriJPf2xOntvOHF3yO7_-qRfjUoFL2s55GX2DGFEuw8ISr8Ctc71WxHgzbZ6d_C8SN46sxKy0blffmhvUznFoUSVcJ7F2N85IehpmrpzjbRXOpWVkwrMlOLktHGU6qK1r3BmvfqeyhvDGMMPAynB_sn_UHXpOowcsj0XNeyCOTCWUiZbiwNs6FTqTFrZlF7ZD3Aq0QVgQq4Qm3RksETToQSuciJA2T2XAFZouyMN-AYTuBlJFUIgwiFYaJMbn2rfQNIkcj_Q78aIcpva35ONKgoTmd-oEd8J8OZOoqJ4itM5ZMi6fuj-sAf6NK-Maruu0kSRstgOJYRsfK2OvNx1JcvnQmkxWmnGAnEN7FCeV2_P7ON2_A_OBseJweH45-deFjHd1ALqJVmHV3E7OGoMmp9Wpl_APC2ArA
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3fT9swELa2TkLjATYGosCGJ-1pUiBp4th5BLqK_WiFBEi8RXFsi0KVVI1bAX89d07K6DrxwGPks53E57vP9vk7Qr5JgCAK06RqIzIP_K3yZMaZ5zPBO7GCQU_wNnJ_EJ9eRr-u2FUTm1M1YZW4hjY1UYSz1Ti5x8rMI-IOwet3YF2AOwwsFoA53pJ3gAJ8VPPQH_yl2uNuew_FPZCP54ea_2tiwS0tkJYuGWnneXrrdXrVyhEWYsDJ7cHUyoP84R86x1d_1Aey1mBSelQr0UfyRhcbZPUZU-EnctN1kR4Umqfn9wWgxmpY0dLQQTnTI3qSgWJhHJ0T6A6rvMSHfmZrBafH4CwVLQsKNenZdWkxv4m7oDXTUHsis4dypCki4E1y2ftxcXLqNWkavDziHeuFLNIZlzqSmnFj4pyrRBhYmBmwDXknUBJARSATljCjlQDIpAIuVc5DtC-ZCbdIqygLvU0otBMIEQnJwyCSYZhonSvfCF8DbtTCb5Pv81FKxzUbRxo0JKdLP7BN_OfjmFq3BWLqfCXL4qm9s23CXqgSvtDV7lxH0sYGgDiU4aEyvPXXp1KYvHgikxW6nMJLALiLE8zsuPPKnvfJylm3l_75Ofi9S97XoQ24P7RHWnYy1Z8BMVn5xc2LR4kHCW0
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=Design+and+Synthesis+of+Novel+Calamitic+and+Discotic+Materials+Based+on+the+Photorefractive+Carbazole+Unit&rft.jtitle=Molecular+crystals+and+liquid+crystals+%28Philadelphia%2C+Pa.+%3A+2003%29&rft.au=Manickam%2C+M.&rft.au=Iqbal%2C+P.&rft.au=Spencer%2C+N.&rft.au=Ashton%2C+P.+R.&rft.date=2010-01-01&rft.pub=Taylor+%26+Francis+Group&rft.issn=1542-1406&rft.eissn=1563-5287&rft.volume=518&rft.issue=1&rft.spage=84&rft.epage=100&rft_id=info:doi/10.1080%2F15421400903568054&rft.externalDocID=457281
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1542-1406&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1542-1406&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1542-1406&client=summon