Synthesis, Self-Assembly, and Solar Cell Performance of N‑Annulated Perylene Diimide Non-Fullerene Acceptors
The synthesis, characterization, and photovoltaic performance of a series of N-annulated PDI materials is presented. Four novel N-annulated PDI compounds are reported, each of which can be synthesized in gram scale without the need for purification using column chromatography. N-Annulation of the PD...
Saved in:
Published in | Chemistry of materials Vol. 28; no. 19; pp. 7098 - 7109 |
---|---|
Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
11.10.2016
|
Online Access | Get full text |
Cover
Loading…
Abstract | The synthesis, characterization, and photovoltaic performance of a series of N-annulated PDI materials is presented. Four novel N-annulated PDI compounds are reported, each of which can be synthesized in gram scale without the need for purification using column chromatography. N-Annulation of the PDI chromophore results in a decrease in electron affinity and lowering of the ionization potential, and renders the chromophore insoluble in organic solvents. Installation of an alkyl group improves the solubility. Single crystal X-ray analysis reveals a bowing of the aromatic backbone and compression of phenyl rings adjacent to the N atom. A brominated N-annulated PDI derivate represents a valuable synthon for creating novel multi-PDI chromophore materials. To demonstrate the utility of the new synthon for making electron transporting materials, a dimerization strategy was employed to create a dimeric PDI material. The PDI dimer has excellent solubility and film forming ability along with energetically deep HOMO and LUMO energy levels. X-ray crystal structure analysis reveals that, despite the isotropic nature of the molecule, only 1-D charge transport pathways are formed. Solar cells based on the new PDI dimer with the standard donor polymer PTB7 gave a high power conversion efficiency of 2.21% for this system. Through N-alkyl chain modification this PCE was increased to 3.13%. Further increases in PCE to 5.54% and 7.55% were achieved by using the more advanced donor polymers PTB7-Th and P3TEA, respectively. The simple yet high performance devices coupled with the highly modular and scalable “acceptor” synthesis make fullerene-free organic solar cells an attractive and cost-effective clean energy technology. |
---|---|
AbstractList | The synthesis, characterization, and photovoltaic performance of a series of N-annulated PDI materials is presented. Four novel N-annulated PDI compounds are reported, each of which can be synthesized in gram scale without the need for purification using column chromatography. N-Annulation of the PDI chromophore results in a decrease in electron affinity and lowering of the ionization potential, and renders the chromophore insoluble in organic solvents. Installation of an alkyl group improves the solubility. Single crystal X-ray analysis reveals a bowing of the aromatic backbone and compression of phenyl rings adjacent to the N atom. A brominated N-annulated PDI derivate represents a valuable synthon for creating novel multi-PDI chromophore materials. To demonstrate the utility of the new synthon for making electron transporting materials, a dimerization strategy was employed to create a dimeric PDI material. The PDI dimer has excellent solubility and film forming ability along with energetically deep HOMO and LUMO energy levels. X-ray crystal structure analysis reveals that, despite the isotropic nature of the molecule, only 1-D charge transport pathways are formed. Solar cells based on the new PDI dimer with the standard donor polymer PTB7 gave a high power conversion efficiency of 2.21% for this system. Through N-alkyl chain modification this PCE was increased to 3.13%. Further increases in PCE to 5.54% and 7.55% were achieved by using the more advanced donor polymers PTB7-Th and P3TEA, respectively. The simple yet high performance devices coupled with the highly modular and scalable “acceptor” synthesis make fullerene-free organic solar cells an attractive and cost-effective clean energy technology. |
Author | Hendsbee, Arthur D Sun, Jon-Paul Law, Wai Kit Yan, He Welch, Gregory C Hill, Ian G Spasyuk, Denis M |
AuthorAffiliation | Department of Chemistry The Hong Kong University of Science and Technology Canadian Light Source Inc University of Calgary Dalhousie University Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration & Reconstruction Department of Physics |
AuthorAffiliation_xml | – name: Department of Chemistry – name: University of Calgary – name: Dalhousie University – name: Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration & Reconstruction – name: The Hong Kong University of Science and Technology – name: Department of Physics – name: Canadian Light Source Inc |
Author_xml | – sequence: 1 givenname: Arthur D surname: Hendsbee fullname: Hendsbee, Arthur D – sequence: 2 givenname: Jon-Paul surname: Sun fullname: Sun, Jon-Paul – sequence: 3 givenname: Wai Kit surname: Law fullname: Law, Wai Kit – sequence: 4 givenname: He surname: Yan fullname: Yan, He – sequence: 5 givenname: Ian G surname: Hill fullname: Hill, Ian G – sequence: 6 givenname: Denis M surname: Spasyuk fullname: Spasyuk, Denis M – sequence: 7 givenname: Gregory C surname: Welch fullname: Welch, Gregory C email: gregory.welch@ucalgary.ca |
BookMark | eNqFkNFKwzAUhoNMcJs-gpAHWGeSNk16WaZTYUxhel3S9JR1pMlIuove-Qq-ok9iy4a3Xh04P99_Dt8MTayzgNA9JUtKGH1QOiz1HtpWdeCXaUlilrErNKWckYgTwiZoSmQmokTw9AbNQjgQQgdUTpHd9bbbQ2jCAu_A1FEeArSl6RdY2QrvnFEer8AY_A6-dr5VVgN2Nd7-fH3n1p7McLQaw96ABfzYNG1TAd46G61PxoAft7nWcOycD7foulYmwN1lztHn-ulj9RJt3p5fV_kmUnFKu4jXiqQSsqyScZUmwKVgICRPRFnKIaSgMh5LzQkrSSbSLNZJIlJJBBOpkHU8R_zcq70LwUNdHH3TKt8XlBSjtGKQVvxJKy7SBo6euTE-uJO3w5f_ML8x83eI |
CitedBy_id | crossref_primary_10_1002_tcr_201800157 crossref_primary_10_1021_acsaem_8b01484 crossref_primary_10_1039_C7TC03171H crossref_primary_10_1002_tcr_201800037 crossref_primary_10_1021_acs_chemmater_6b04862 crossref_primary_10_1039_D4CC00176A crossref_primary_10_1002_ejoc_201901319 crossref_primary_10_1002_tcr_202200208 crossref_primary_10_1007_s10854_019_02019_z crossref_primary_10_1016_j_dyepig_2018_09_022 crossref_primary_10_1016_j_jssc_2021_122687 crossref_primary_10_1039_C9TA09260A crossref_primary_10_1016_j_ijbiomac_2021_08_006 crossref_primary_10_1039_D2CC02427F crossref_primary_10_1039_C7TA00318H crossref_primary_10_1002_cplu_201700502 crossref_primary_10_1039_C7SE00056A crossref_primary_10_1021_acs_jpcc_1c01964 crossref_primary_10_1002_ejoc_201801383 crossref_primary_10_1039_C8NJ02566E crossref_primary_10_1021_acsaem_0c01587 crossref_primary_10_3390_synbio2010002 crossref_primary_10_1002_chem_201701066 crossref_primary_10_1039_D2CC04784E crossref_primary_10_1007_s11664_022_09728_y crossref_primary_10_1016_j_dyepig_2019_04_027 crossref_primary_10_1002_asia_201701493 crossref_primary_10_1002_cphc_201900793 crossref_primary_10_1039_D3TC03695B crossref_primary_10_1002_nano_202000089 crossref_primary_10_1021_acs_chemrev_2c00905 crossref_primary_10_1039_C7TA06804B crossref_primary_10_1039_C8NJ06491A crossref_primary_10_1039_C6TC05171E crossref_primary_10_1088_2058_8585_aca166 crossref_primary_10_1021_acs_jpclett_3c02392 crossref_primary_10_1039_D3CE01146A crossref_primary_10_1039_D3TC02376A crossref_primary_10_3390_molecules23040931 crossref_primary_10_1016_j_orgel_2017_04_032 crossref_primary_10_1021_acsaem_8b00929 crossref_primary_10_1039_C9SM00716D crossref_primary_10_1039_C7TC05631A crossref_primary_10_1039_D1SC05465A crossref_primary_10_1002_chem_202304333 crossref_primary_10_1002_tcr_201800114 crossref_primary_10_3389_fchem_2018_00414 crossref_primary_10_1016_j_dyepig_2019_107970 crossref_primary_10_1039_D0ME00081G crossref_primary_10_1039_C7OB00362E crossref_primary_10_1016_j_synthmet_2019_02_010 crossref_primary_10_1039_C6TA09607G crossref_primary_10_1002_aenm_201602269 crossref_primary_10_1021_acsaem_8b01793 crossref_primary_10_1039_D1TC03034E crossref_primary_10_1039_C7NJ04285J crossref_primary_10_1021_acsaem_8b01433 crossref_primary_10_1039_C6TC05066B crossref_primary_10_1016_j_dyepig_2018_09_051 crossref_primary_10_1039_C6TC05107C crossref_primary_10_1039_C8CE01806E crossref_primary_10_1021_acs_jpcc_8b05086 crossref_primary_10_1021_acsami_0c11809 crossref_primary_10_1039_C6CC08939A crossref_primary_10_1039_C7TC05245F crossref_primary_10_1002_ejoc_201801055 crossref_primary_10_1039_D3NJ05107B crossref_primary_10_1039_D1TC03873G crossref_primary_10_1016_j_jechem_2019_03_007 crossref_primary_10_1039_C7CC05836E crossref_primary_10_1002_chem_202102318 crossref_primary_10_1039_D3TA04925F crossref_primary_10_1039_D2QM00299J crossref_primary_10_1002_solr_201700123 crossref_primary_10_1021_acs_jpcc_6b12174 crossref_primary_10_1038_s41560_018_0181_5 crossref_primary_10_1039_D4TC01104J crossref_primary_10_1002_chem_201705290 crossref_primary_10_1039_D0RA10346B crossref_primary_10_1002_marc_201700555 crossref_primary_10_1021_acs_chemmater_7b01650 crossref_primary_10_1002_asia_201701424 crossref_primary_10_3390_ma13092148 crossref_primary_10_3390_molecules25225373 crossref_primary_10_3389_fchem_2018_00328 crossref_primary_10_1016_j_xcrp_2021_100390 crossref_primary_10_1039_D0CC05528J crossref_primary_10_1039_D2PY01008A crossref_primary_10_3390_molecules24234406 crossref_primary_10_1021_acsami_0c16238 crossref_primary_10_1039_D1NJ04423K crossref_primary_10_1021_acsaem_9b01978 crossref_primary_10_1002_jctb_6894 crossref_primary_10_1002_smtd_201800081 crossref_primary_10_1039_C8TC04926B crossref_primary_10_3389_fchem_2018_00613 crossref_primary_10_1039_C8QO01368C crossref_primary_10_1039_D3QO01914D crossref_primary_10_1021_acs_orglett_8b02650 crossref_primary_10_1088_1674_4926_41_9_091708 crossref_primary_10_1002_smll_201701120 crossref_primary_10_1002_cplu_202400131 crossref_primary_10_1039_C9NJ01574D crossref_primary_10_1016_j_dyepig_2017_09_032 crossref_primary_10_1021_acs_orglett_2c04220 crossref_primary_10_1039_D3CP03888B crossref_primary_10_1002_adfm_202410077 crossref_primary_10_1021_acs_jpca_0c00346 crossref_primary_10_1016_j_dyepig_2017_06_050 crossref_primary_10_1021_acs_chemmater_7b01718 crossref_primary_10_1002_solr_201800143 crossref_primary_10_1021_acsami_3c11174 crossref_primary_10_1039_C8SC03525C crossref_primary_10_1039_D0TC03610B crossref_primary_10_1039_D2NJ00955B crossref_primary_10_1002_smll_201801793 crossref_primary_10_1039_D0RA07050E crossref_primary_10_1039_C8TC00089A crossref_primary_10_1055_s_0040_1714283 crossref_primary_10_1016_j_progpolymsci_2019_101175 crossref_primary_10_1016_j_jtice_2017_11_025 crossref_primary_10_1021_acsami_1c15251 crossref_primary_10_1039_D2SC04387D crossref_primary_10_1016_j_joule_2017_10_006 crossref_primary_10_1002_bio_4166 crossref_primary_10_1002_cctc_202301033 crossref_primary_10_1021_acsaelm_9b00328 crossref_primary_10_1021_acsami_2c10466 crossref_primary_10_1039_C7SE00345E crossref_primary_10_1016_j_orgel_2017_05_004 crossref_primary_10_1016_j_dyepig_2017_07_060 crossref_primary_10_1039_D3SC05514K crossref_primary_10_1039_D2TC02999E crossref_primary_10_1016_j_cclet_2017_08_025 crossref_primary_10_1002_tcr_202100202 crossref_primary_10_1039_D2TC03224D crossref_primary_10_1002_asia_201700419 crossref_primary_10_1039_D0CC04556J crossref_primary_10_1002_ajoc_202000106 crossref_primary_10_1016_j_mtnano_2018_04_005 crossref_primary_10_1002_solr_201900453 crossref_primary_10_1002_aenm_201801699 crossref_primary_10_1021_acsapm_9b00433 crossref_primary_10_1039_C7CC03682E crossref_primary_10_1039_C7TC04726F crossref_primary_10_1016_j_jlumin_2017_07_019 crossref_primary_10_1039_C7TC05261H crossref_primary_10_1002_chem_201705480 crossref_primary_10_1021_acsami_8b06126 crossref_primary_10_1039_C9TC02150G crossref_primary_10_1039_C7TA05282K crossref_primary_10_1039_C7RA01311F crossref_primary_10_3390_colorants2010011 crossref_primary_10_1021_acs_chemrev_7b00535 crossref_primary_10_1039_D0QM00109K crossref_primary_10_1039_D0MH00785D crossref_primary_10_1021_acs_chemmater_2c03122 crossref_primary_10_1002_aenm_202002678 crossref_primary_10_1039_C8TC02823K crossref_primary_10_1007_s40843_022_2339_9 crossref_primary_10_1016_j_dyepig_2024_112038 crossref_primary_10_1039_D1NJ02130C crossref_primary_10_1039_C9OB02751C crossref_primary_10_1039_C8CC06446F crossref_primary_10_3390_molecules29112538 crossref_primary_10_1002_qua_27092 crossref_primary_10_1021_acs_joc_8b02899 crossref_primary_10_1016_j_apmt_2020_100799 crossref_primary_10_1016_j_synthmet_2022_117088 crossref_primary_10_1002_adem_202201437 crossref_primary_10_1039_D0NJ01733G crossref_primary_10_1039_C8TC02701C crossref_primary_10_1007_s11696_017_0361_y crossref_primary_10_1016_j_dyepig_2018_07_037 crossref_primary_10_1039_D0TA11197J crossref_primary_10_1007_s11426_021_1171_4 crossref_primary_10_1021_acsenergylett_8b00366 crossref_primary_10_1002_slct_201800363 crossref_primary_10_1016_j_molstruc_2019_02_042 crossref_primary_10_1021_acsami_2c12281 crossref_primary_10_1016_j_orgel_2020_105976 crossref_primary_10_1002_adfm_201902478 crossref_primary_10_1016_j_nanoen_2022_108017 crossref_primary_10_1016_j_dyepig_2018_12_015 crossref_primary_10_1021_acsami_8b19563 crossref_primary_10_1002_tcr_201800180 crossref_primary_10_1039_D0CC00337A crossref_primary_10_1039_C9CC10006G crossref_primary_10_1002_cssc_202002784 crossref_primary_10_1021_jacs_1c09481 crossref_primary_10_1039_C7TA02582C crossref_primary_10_1016_j_mser_2018_01_001 crossref_primary_10_1039_C8QM00487K crossref_primary_10_1039_D0TC02284E crossref_primary_10_3390_molecules25061402 crossref_primary_10_1021_acsomega_0c01217 crossref_primary_10_1021_acsami_9b19549 crossref_primary_10_1002_aenm_201800204 crossref_primary_10_1021_acs_chemrev_1c00449 crossref_primary_10_1016_j_rinp_2020_103633 |
Cites_doi | 10.1039/C5EE03727A 10.1016/S1369-7021(13)70013-0 10.1039/c3ee41096j 10.1039/C5TC00865D 10.1002/chem.200600889 10.1038/nphoton.2012.190 10.1016/j.dyepig.2013.01.020 10.1002/adma.201104439 10.1021/am5016765 10.1039/C3CC47204C 10.1021/am201616r 10.1063/1.2885712 10.1021/jacs.5b06414 10.1002/adma.201004554 10.1002/adma.200903528 10.1007/s10895-015-1725-8 10.1039/C5RA13188J 10.1002/aenm.201000024 10.1021/cm202852f 10.1002/(SICI)1099-0690(200001)2000:2<365::AID-EJOC365>3.3.CO;2-I 10.1021/ja508814z 10.1021/am5063844 10.1039/C5TA04310G 10.1021/acsami.6b03926 10.1039/B512373A 10.1039/c2ob25119a 10.1021/jo070367n 10.1016/j.orgel.2013.06.016 10.1038/nenergy.2016.89 10.1021/cm501513n 10.1021/acs.chemmater.5b04339 10.1021/ma500829r 10.1002/aenm.201400420 10.1021/jo0503299 10.1021/cm4020805 10.1039/c3tb21801e 10.1002/adfm.201500837 10.1016/j.orgel.2012.06.002 10.1039/C5RA17715D 10.1016/j.mattod.2013.08.013 10.1021/ja5092613 10.1039/C6TA02045C 10.1002/adma.201500647 10.1039/c3ra22926b 10.1039/C5RA02468D 10.1002/aenm.201200372 10.1021/jacs.5b11149 10.1002/adma.201001402 10.1002/adma.201401992 10.1039/C4CP04161E 10.1039/C3TA14236A 10.1021/ja071760d 10.1021/cm300747v 10.1039/C4EE02990A 10.1021/cm1023019 10.1039/C4MH00042K 10.1039/C6CP01269H 10.1021/jo901285k 10.1021/ol0167356 10.1002/pssa.201127592 10.1002/adma.201305999 10.1038/ncomms9242 10.1080/00032719.2015.1122028 10.1039/c3sc51841h 10.1039/C3MH00098B 10.1038/nature02498 10.1016/j.orgel.2016.05.012 10.1002/adma.201400525 10.1002/cber.19881210205 10.1021/acssuschemeng.6b00554 10.1038/nphoton.2012.11 10.1002/adma.201400384 10.1039/C5TC01877C |
ContentType | Journal Article |
Copyright | Copyright © 2016 American Chemical
Society |
Copyright_xml | – notice: Copyright © 2016 American Chemical Society |
DBID | AAYXX CITATION |
DOI | 10.1021/acs.chemmater.6b03292 |
DatabaseName | CrossRef |
DatabaseTitle | CrossRef |
DatabaseTitleList | |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Engineering Chemistry |
EISSN | 1520-5002 |
EndPage | 7109 |
ExternalDocumentID | 10_1021_acs_chemmater_6b03292 b42013154 |
GroupedDBID | 29B 53G 55A 5GY 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACJ ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ CS3 DU5 EBS ED ED~ EJD F5P GNL IH9 JG JG~ LG6 P2P ROL TN5 TWZ UI2 UPT VF5 VG9 W1F X YZZ -~X .K2 4.4 5VS AAHBH AAYXX ABJNI ABQRX ADHLV AGXLV AHGAQ BAANH CITATION CUPRZ GGK |
ID | FETCH-LOGICAL-a361t-5fa068e99d83d64e5872e78547bb85fa1ea9538c502b097693c447680727678f3 |
IEDL.DBID | ACS |
ISSN | 0897-4756 |
IngestDate | Fri Dec 06 05:39:09 EST 2024 Thu Aug 27 13:42:36 EDT 2020 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 19 |
Language | English |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-a361t-5fa068e99d83d64e5872e78547bb85fa1ea9538c502b097693c447680727678f3 |
PageCount | 12 |
ParticipantIDs | crossref_primary_10_1021_acs_chemmater_6b03292 acs_journals_10_1021_acs_chemmater_6b03292 |
ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N ACJ VG9 W1F ACS AEESW AFEFF ABMVS ABUCX IH9 AQSVZ ED~ UI2 |
PublicationCentury | 2000 |
PublicationDate | 2016-10-11 |
PublicationDateYYYYMMDD | 2016-10-11 |
PublicationDate_xml | – month: 10 year: 2016 text: 2016-10-11 day: 11 |
PublicationDecade | 2010 |
PublicationTitle | Chemistry of materials |
PublicationTitleAlternate | Chem. Mater |
PublicationYear | 2016 |
Publisher | American Chemical Society |
Publisher_xml | – name: American Chemical Society |
References | ref9/cit9 ref45/cit45 ref3/cit3 ref27/cit27 ref63/cit63 ref56/cit56 ref16/cit16 ref52/cit52 ref23/cit23 ref8/cit8 ref31/cit31 ref59/cit59 ref2/cit2 ref34/cit34 ref71/cit71 ref37/cit37 ref20/cit20 ref48/cit48 ref60/cit60 ref17/cit17 ref10/cit10 ref35/cit35 ref53/cit53 ref19/cit19 ref21/cit21 ref42/cit42 ref46/cit46 ref49/cit49 ref13/cit13 ref61/cit61 ref67/cit67 ref24/cit24 ref38/cit38 ref50/cit50 ref64/cit64 ref54/cit54 ref6/cit6 ref36/cit36 ref18/cit18 ref65/cit65 ref11/cit11 ref25/cit25 ref29/cit29 ref72/cit72 ref32/cit32 ref39/cit39 ref14/cit14 ref57/cit57 ref5/cit5 ref51/cit51 ref43/cit43 ref28/cit28 ref40/cit40 ref68/cit68 ref26/cit26 ref55/cit55 ref73/cit73 ref69/cit69 ref12/cit12 ref15/cit15 ref62/cit62 ref66/cit66 ref41/cit41 ref58/cit58 ref22/cit22 ref33/cit33 ref4/cit4 ref30/cit30 ref47/cit47 ref1/cit1 ref44/cit44 ref70/cit70 ref7/cit7 |
References_xml | – ident: ref41/cit41 doi: 10.1039/C5EE03727A – ident: ref20/cit20 doi: 10.1016/S1369-7021(13)70013-0 – ident: ref44/cit44 doi: 10.1039/c3ee41096j – ident: ref32/cit32 doi: 10.1039/C5TC00865D – ident: ref57/cit57 doi: 10.1002/chem.200600889 – ident: ref68/cit68 doi: 10.1038/nphoton.2012.190 – ident: ref16/cit16 doi: 10.1016/j.dyepig.2013.01.020 – ident: ref49/cit49 doi: 10.1002/adma.201104439 – ident: ref10/cit10 doi: 10.1021/am5016765 – ident: ref19/cit19 doi: 10.1039/C3CC47204C – ident: ref11/cit11 doi: 10.1021/am201616r – ident: ref12/cit12 doi: 10.1063/1.2885712 – ident: ref36/cit36 doi: 10.1021/jacs.5b06414 – ident: ref59/cit59 doi: 10.1002/adma.201004554 – ident: ref67/cit67 doi: 10.1002/adma.200903528 – ident: ref9/cit9 doi: 10.1007/s10895-015-1725-8 – ident: ref34/cit34 doi: 10.1039/C5RA13188J – ident: ref65/cit65 doi: 10.1002/aenm.201000024 – ident: ref50/cit50 doi: 10.1021/cm202852f – ident: ref39/cit39 doi: 10.1002/(SICI)1099-0690(200001)2000:2<365::AID-EJOC365>3.3.CO;2-I – ident: ref18/cit18 doi: 10.1021/ja508814z – ident: ref6/cit6 doi: 10.1021/am5063844 – ident: ref28/cit28 doi: 10.1039/C5TA04310G – ident: ref71/cit71 doi: 10.1021/acsami.6b03926 – ident: ref60/cit60 doi: 10.1039/B512373A – ident: ref7/cit7 doi: 10.1039/c2ob25119a – ident: ref45/cit45 doi: 10.1021/jo070367n – ident: ref62/cit62 doi: 10.1016/j.orgel.2013.06.016 – ident: ref73/cit73 doi: 10.1038/nenergy.2016.89 – ident: ref70/cit70 doi: 10.1021/cm501513n – ident: ref29/cit29 doi: 10.1021/acs.chemmater.5b04339 – ident: ref69/cit69 doi: 10.1021/ma500829r – ident: ref30/cit30 doi: 10.1002/aenm.201400420 – ident: ref40/cit40 doi: 10.1021/jo0503299 – ident: ref55/cit55 doi: 10.1021/cm4020805 – ident: ref5/cit5 doi: 10.1039/c3tb21801e – ident: ref15/cit15 doi: 10.1002/adfm.201500837 – ident: ref14/cit14 doi: 10.1016/j.orgel.2012.06.002 – ident: ref27/cit27 doi: 10.1039/C5RA17715D – ident: ref63/cit63 doi: 10.1016/j.mattod.2013.08.013 – ident: ref4/cit4 doi: 10.1021/ja5092613 – ident: ref17/cit17 doi: 10.1039/C6TA02045C – ident: ref66/cit66 doi: 10.1002/adma.201500647 – ident: ref25/cit25 doi: 10.1039/c3ra22926b – ident: ref43/cit43 doi: 10.1039/C5RA02468D – ident: ref64/cit64 doi: 10.1002/aenm.201200372 – ident: ref3/cit3 doi: 10.1021/jacs.5b11149 – ident: ref1/cit1 doi: 10.1002/adma.201001402 – ident: ref37/cit37 doi: 10.1002/adma.201401992 – ident: ref56/cit56 doi: 10.1039/C4CP04161E – ident: ref24/cit24 doi: 10.1039/C3TA14236A – ident: ref33/cit33 doi: 10.1021/ja071760d – ident: ref47/cit47 doi: 10.1021/cm300747v – ident: ref72/cit72 doi: 10.1039/C4EE02990A – ident: ref26/cit26 doi: 10.1021/cm1023019 – ident: ref23/cit23 doi: 10.1039/C4MH00042K – ident: ref51/cit51 doi: 10.1039/C6CP01269H – ident: ref53/cit53 doi: 10.1021/jo901285k – ident: ref48/cit48 doi: 10.1021/ol0167356 – ident: ref13/cit13 doi: 10.1002/pssa.201127592 – ident: ref22/cit22 doi: 10.1002/adma.201305999 – ident: ref2/cit2 doi: 10.1038/ncomms9242 – ident: ref8/cit8 doi: 10.1080/00032719.2015.1122028 – ident: ref35/cit35 doi: 10.1039/c3sc51841h – ident: ref58/cit58 doi: 10.1039/C3MH00098B – ident: ref54/cit54 doi: 10.1038/nature02498 – ident: ref52/cit52 doi: 10.1016/j.orgel.2016.05.012 – ident: ref31/cit31 doi: 10.1002/adma.201400525 – ident: ref38/cit38 doi: 10.1002/cber.19881210205 – ident: ref42/cit42 doi: 10.1021/acssuschemeng.6b00554 – ident: ref21/cit21 doi: 10.1038/nphoton.2012.11 – ident: ref61/cit61 doi: 10.1002/adma.201400384 – ident: ref46/cit46 doi: 10.1039/C5TC01877C |
SSID | ssj0011028 |
Score | 2.639188 |
Snippet | The synthesis, characterization, and photovoltaic performance of a series of N-annulated PDI materials is presented. Four novel N-annulated PDI compounds are... |
SourceID | crossref acs |
SourceType | Aggregation Database Publisher |
StartPage | 7098 |
Title | Synthesis, Self-Assembly, and Solar Cell Performance of N‑Annulated Perylene Diimide Non-Fullerene Acceptors |
URI | http://dx.doi.org/10.1021/acs.chemmater.6b03292 |
Volume | 28 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlZ1LSwMxEMdDqQf14Ft8k4MnMW32kd3kWFaLCBahCt6WJJtgcbuVbj3Uk1_Br-gncdJua0EUvW7YEGaz-f-GycwgdKq5pCZWjESUaxLKwBIZcUMcbHABiCJ9l-B804mu7sPrB_ZQQ80fIvi-15QajP9o-gBwZtiIFA18AWfukh-DC-5YKOnOwwZOLSfYKGISxiyapez8NI2TJF0uSNKCtrTX0e0sQ2d6peSp8TJSDf36vWDjX5e9gdYqzsSt6cbYRDVTbKHlZNbebQutLlQi3EZFd1wACpa98hx3TW6JCwb3VT4-x7LIcNc5wDgxeY5vvzIN8MDizsfbu6vRn8MCMjc4Bhkz-KLX6_cygzuDgjgvd9KDBbe0u0QzGJY76L59eZdckaoVA5FB5I0Is5LCJxQi40EWhYbx2DcxZ2GsFIdBz0gBR6dm1FdUuP6KOgzBk6GARyCHNthF9WJQmD2ENbOKxUJxz9owy7jk1gDDSC-jQlPJ9tEZ2C6tfqUynUTJfS91D-cGTSuD7qPG7NOlz9PyHL-_cPCf2Q_RCvBR5KTK845QfTR8McfAICN1Mtl3n_vP2eE |
link.rule.ids | 314,780,784,2765,27076,27924,27925,56738,56788 |
linkProvider | American Chemical Society |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NThsxEB4hOEAPhVKqAoX60FOFg_fHXvuIUlDaQlQpILitbK8tRWw2KBsO4cQr8Io8CeMlCVElkLja2tHs-Of7RuOZAfhhpWYuM5wKJi1NdeKpFtLRQDakQoqi45DgfNYVnYv0zxW_WgIxy4VBJWqUVDdB_JfqAtFhGMPfGCCPc6OWMCyJFV69Kzy0rQyUqN2bRw8CaDbsUWU0zbiYZe68JiYgk60XkGkBYk7W4XKuXPOy5Lp1OzYte_df3cb3a78BH6eskxw9b5NPsOSqTVhtz5q9bcKHhbqEn6HqTSokhnW_PiA9V3oaQsMDU04OiK4K0gvuMGm7siT_XvIOyNCT7uP9Q6jYX6ICRZicIKg58qvfH_QLR7rDigaft-nIQo5seFIzHNVbcHFyfN7u0GljBqoTEY0p95rhgipVyKQQqeMyi10meZoZI3EyclrhRWo5iw1ToduiTVP0axiSJQRHn3yB5WpYua9ALPeGZ8rIyPu0KKSW3iGj0VHBlGWab8NPtF0-PVh13sTM4ygPg3OD5lODbkNrtoL5zXOxjrc_2HmP9O-w2jk_O81Pf3f_7sIaMicRQCyKvsHyeHTr9pCdjM1-sxWfALLr4k4 |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LahsxFBUlhT4WbZM0NE0fWnRVIkfz0Iy0NHZN2iYm4AYCXQx6gul4bDzOwl31F_qL_ZLcOx47JtBAu5XQRdKVdI64L0I-WKm5z41gGZeWpToJTGfSMyQbUgFF0TEGOJ8Ps9PL9MuVuGq9KjEWBiZRg6S6MeLjrZ650GYYiE6wHZYyAS7n553M8CRW8Pw-FPDiojtXtzfaWBAQOBsGqXKW5iJbR-_8TQyik6230GkLZgbPyffNBBvvkh-d64Xp2J93cjf-3wpekGct-6Td1XHZJQ98tUce99ZF3_bI0638hPukGi0rIIj1uD6mI18GhibiiSmXx1RXjo7wW0x7vizpxW38AZ0GOvzz6zdm7i9hAg47lwBunvbH48nYeTqcVgz_vk1lFtq16FozndcvyeXg07feKWsLNDCdZNGCiaA5KFYpJxOXpV7IPPa5FGlujITOyGsFD6oVPDZcYdVFm6bwv-FAmkBlITkgO9W08q8ItSIYkSsjoxBS56SWwQOz0ZHjynItDslH2LuivWB10djO46jAxs2GFu2GHpLOWovFbJW04_4Br_9F-nvy6KI_KM4-D78ekSdAoDLEsih6Q3YW82v_FkjKwrxrTuMNB4Xk0Q |
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=Synthesis%2C+Self-Assembly%2C+and+Solar+Cell+Performance+of+N%E2%80%91Annulated+Perylene+Diimide+Non-Fullerene+Acceptors&rft.jtitle=Chemistry+of+materials&rft.au=Hendsbee%2C+Arthur+D&rft.au=Sun%2C+Jon-Paul&rft.au=Law%2C+Wai+Kit&rft.au=Yan%2C+He&rft.date=2016-10-11&rft.pub=American+Chemical+Society&rft.issn=0897-4756&rft.eissn=1520-5002&rft.volume=28&rft.issue=19&rft.spage=7098&rft.epage=7109&rft_id=info:doi/10.1021%2Facs.chemmater.6b03292&rft.externalDocID=b42013154 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0897-4756&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0897-4756&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0897-4756&client=summon |