Phenylene-Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure-Property Relationship.
density functional calculations
donor-acceptor systems
dyes
organic photovoltaics
perylene monoimide
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Apr 2022
22 Apr 2022
Historique:
received:
27
01
2022
pubmed:
27
2
2022
medline:
27
2
2022
entrez:
26
2
2022
Statut:
ppublish
Résumé
A series of non-fullerene acceptors based on perylene monoimides coupled in the peri position through phenylene linkers were synthesized via Suzuki-coupling reactions. Various substitution patterns were investigated using density functional theory (DFT) calculations in combination with experimental data to elucidate the geometry and their optical and electrochemical properties. Further investigations of the bulk properties with grazing incidence wide angle X-ray scattering (GIWAXS) gave insight into the stacking behavior of the acceptor thin films. Electrochemical and morphological properties correlate with the photovoltaic performance of devices with the polymeric donor PBDB-T and a maximum efficiency of 3.17 % was reached. The study gives detailed information about structure-property relationships of perylene-linker-perylene compounds.
Identifiants
pubmed: 35218252
doi: 10.1002/chem.202200276
pmc: PMC9313791
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200276Subventions
Organisme : Austrian Science Fund
ID : M2738
Organisme : Österreichischen Akademie der Wissenschaften
ID : MOCHEM
Organisme : Klima- und Energiefonds
ID : 865 072
Organisme : CERIC-ERIC Consortium
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
J Org Chem. 2002 Mar 8;67(5):1663-8
pubmed: 11871900
Chem Commun (Camb). 2006 Nov 13;(42):4440-2
pubmed: 17057870
J Appl Crystallogr. 2011 Dec 1;44(Pt 6):1281-1284
pubmed: 22477785
Acta Crystallogr D Biol Crystallogr. 2009 Feb;65(Pt 2):148-55
pubmed: 19171970
J Org Chem. 2017 Jun 2;82(11):5926-5931
pubmed: 28489380
J Am Chem Soc. 2017 Nov 15;139(45):16092-16095
pubmed: 29112393
Phys Chem Chem Phys. 2020 Jan 28;22(4):2379-2385
pubmed: 31935005
Chemistry. 2022 Apr 22;28(23):e202200276
pubmed: 35218252
Chem Rev. 2018 Apr 11;118(7):3447-3507
pubmed: 29557657
Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1176-80
pubmed: 25469476
Chem Rev. 2010 May 12;110(5):2641-84
pubmed: 20356094
Br J Surg. 2021 Sep 27;108(9):1056-1063
pubmed: 33761533
Chem Commun (Camb). 2014 Dec 4;50(93):14512-5
pubmed: 25308466
Phys Rev Lett. 2004 Mar 12;92(10):103001
pubmed: 15089202
J Chem Theory Comput. 2009 Mar 10;5(3):540-54
pubmed: 26610221
Chem Commun (Camb). 2020 Sep 29;56(77):11433-11436
pubmed: 32845952
Adv Mater. 2017 Feb;29(7):
pubmed: 27922731
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
J Mater Chem A Mater. 2021 Dec 15;10(6):2888-2906
pubmed: 35223040
J Comput Chem. 2012 Feb 15;33(5):580-92
pubmed: 22162017
Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8
pubmed: 25537383
ACS Appl Energy Mater. 2021 Nov 22;4(11):11899-11981
pubmed: 35856015
Acc Chem Res. 2021 May 4;54(9):2227-2237
pubmed: 33852280
Org Biomol Chem. 2005 Mar 21;3(6):985-95
pubmed: 15750640
J Phys Chem Lett. 2014 May 1;5(9):1608-15
pubmed: 26270104
Adv Mater. 2012 Feb 2;24(5):613-36
pubmed: 22228467
Acta Crystallogr A. 1995 Jan 1;51 ( Pt 1):33-8
pubmed: 7702794
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8
pubmed: 25567568
J Org Chem. 2002 Aug 9;67(16):5733-8
pubmed: 12153276
J Am Chem Soc. 2008 Oct 1;130(39):12858-9
pubmed: 18767851
Nat Mater. 2010 Jan;9(1):31-5
pubmed: 19946281
Angew Chem Int Ed Engl. 2009;48(24):4402-5
pubmed: 19431175
J Org Chem. 2008 Aug 15;73(16):6142-7
pubmed: 18642952
Chem Rev. 2018 Aug 8;118(15):7069-7163
pubmed: 29664617
Chem Commun (Camb). 2020 Apr 7;56(27):3824-3838
pubmed: 32211710
Acc Chem Res. 2021 Feb 2;54(3):642-653
pubmed: 33289387
J Am Chem Soc. 2012 Aug 1;134(30):12855-60
pubmed: 22734631
Chem Rev. 2012 Apr 11;112(4):2208-67
pubmed: 22111507
Chemistry. 2021 Aug 25;27(48):12362-12370
pubmed: 34152046
J Appl Crystallogr. 2020 Feb 01;53(Pt 1):226-235
pubmed: 32047413
J Appl Crystallogr. 2011 Dec 1;44(Pt 6):1259-1263
pubmed: 22199401