Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors

Chemical Science
Patrick E HartnettTobin J Marks

Abstract

A series of perylenediimide (PDI) dimers are evaluated as acceptors for organic photovoltaic (OPV) cells. The materials are characterized using a wide variety of physical and computational techniques. These dimers are first linked at the bay position of each PDI molecule via an aromatic spacer; subsequent photocyclization affords ring-fused dimers. Thus, photocyclization of the thiophene-linked dimer 2,5-bis-[N,N'-bis-perylenediimide-1-yl]-thiophene (T1) affords the twisted acceptor [2,3-b:2',3'-d]-bis-[N,N'-bis-perylenediimide-1,12-yl]-thiophene (T2), while photocyclization of the thienothiophene-linked dimer, 2,5-bis-[N,N'-bis-perylenediimide-1-yl]-thienothiophene (TT1) affords the planar acceptor [2,3-b:2',3'-d]-bis-[N,N'-bis-perylenediimide-1,12-yl]-thienothiophene (TT2). Furthermore, a dimer linked by a phenylene group, 1,4-bis-[N,N'-bis-perylenediimide-1-yl]-benzene (Ph1), can be selectively photocyclized to form either the twisted dimer, [1,2:3,4]-bis-[N,N'-bis-perylenediimide-1,12-yl]-benzene (Ph1a) or the planar dimer [1,2:4,5]-bis-[N,N'-bis-perylenediimide-1,12-yl]-benzene (Ph2b). Ring-fusion results in increased electronic coupling between the PDI units, and increased space-charge limited thin film electron mobility....Continue Reading

References

Aug 9, 2002·Journal of the American Chemical Society·Tamar van der BoomMichael R Wasielewski
Nov 6, 2003·Journal of the American Chemical Society·Amit Babel, Samson A Jenekhe
Sep 17, 2004·Angewandte Chemie·Lawrence T Scott
Feb 9, 2006·Journal of the American Chemical Society·Michael J TauberMichael R Wasielewski
Jun 1, 2006·Journal of the American Chemical Society·Kaushik BalakrishnanLing Zang
Apr 13, 2007·Chemical Reviews·Serap GünesNiyazi Serdar Sariciftci
Aug 19, 2007·Journal of the American Chemical Society·Hualei QianDaoben Zhu
Nov 28, 2008·Journal of the American Chemical Society·Hualei QianZhaohui Wang
Nov 6, 2009·Journal of the American Chemical Society·Ryan D Pensack, John B Asbury
Dec 3, 2009·Journal of Applied Crystallography·Detlef-M Smilgies
May 21, 2010·Physical Review Letters·Justin M HodgkissRichard H Friend
Dec 15, 2010·Advanced Materials·Xiaowei ZhanSeth R Marder
Feb 22, 2011·Environmental Science & Technology·Annick AnctilBrian J Landi
Mar 26, 2011·Chemical Communications : Chem Comm·Frank Würthner, Matthias Stolte
Jun 22, 2011·Journal of the American Chemical Society·Thomas W HolcombeJean M J Fréchet
Jan 10, 2012·Advanced Materials·Chen Li, Henrike Wonneberger
Jun 22, 2013·Advanced Materials·Alexander SharenkoGuillermo C Bazan
Dec 7, 2013·Chemical Communications : Chem Comm·Wei JiangZhaohui Wang
Jan 28, 2014·Journal of the American Chemical Society·Brett M SavoieMark A Ratner
Apr 2, 2014·Advanced Materials·Jean RoncaliPhilippe Blanchard
May 21, 2014·Journal of the American Chemical Society·Yu ZhongColin Nuckolls
Jul 23, 2014·Accounts of Chemical Research·Brett M SavoieMark A Ratner
Sep 30, 2014·Journal of the American Chemical Society·Haiyan LiSamson A Jenekhe
Oct 2, 2014·Physical Chemistry Chemical Physics : PCCP·Eric A MarguliesMichael R Wasielewski
Oct 15, 2014·Journal of the American Chemical Society·Yu ZhongColin Nuckolls
Oct 29, 2014·Journal of the American Chemical Society·Patrick E HartnettTobin J Marks
Apr 10, 2015·The Journal of Physical Chemistry. a·Samuel W EatonMichael R Wasielewski
Jun 2, 2015·Physical Chemistry Chemical Physics : PCCP·Gregory J Dutton, Steven W Robey
Aug 12, 2015·The Journal of Physical Chemistry Letters·Nicholas E JacksonMark A Ratner
Aug 19, 2015·Journal of the American Chemical Society·Dan SunZhaohui Wang
Mar 7, 2013·The Journal of Physical Chemistry Letters·Alexander SchubertVolker Engel
Sep 6, 2012·The Journal of Physical Chemistry Letters·Sridhar RajaramK S Narayan

❮ Previous
Next ❯

Citations

Feb 5, 2019·Angewandte Chemie·Maksim NavakouskiMarcin Stępień
Apr 24, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Zhongrong TianWeiwei Li
Jul 26, 2019·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
Dec 3, 2016·The Journal of Chemical Physics·Nicholas E JacksonMark A Ratner
Oct 8, 2016·Angewandte Chemie·Nathaniel J SchusterColin Nuckolls
Nov 21, 2017·Macromolecular Rapid Communications·Fuchuan LiuShiming Zhang
Feb 15, 2018·Chemistry, an Asian Journal·Zetong MaZhaohui Wang
Feb 19, 2019·Chemical Science·Margarita MiltonColin Nuckolls
Mar 21, 2017·Polymers·Tanwistha GhoshVijayakumar C Nair
Jul 25, 2017·Small·Shuixing LiHongzheng Chen
Dec 8, 2017·Angewandte Chemie·Lei YangHui Huang
Jun 12, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yuvraj Patil, Rajneesh Misra
Jun 3, 2017·Chemistry, an Asian Journal·Wanning LiJianhui Hou
Jul 3, 2019·Angewandte Chemie·Anthony JollyJean-François Morin
Dec 15, 2017·Chemical Communications : Chem Comm·Junhui MiaoLixiang Wang
May 20, 2021·Physical Chemistry Chemical Physics : PCCP·Tobias KochNikos L Doltsinis
Dec 28, 2016·Journal of the American Chemical Society·Patrick E HartnettMichael R Wasielewski
Sep 27, 2018·Organic Letters·Jiajun WuHui-Jun Zhang
Jan 23, 2019·ACS Applied Materials & Interfaces·Han HanDahui Zhao
Apr 22, 2017·ACS Applied Materials & Interfaces·Jenna L LogsdonMichael R Wasielewski
May 11, 2017·The Journal of Organic Chemistry·Yu HuYiwang Chen
Mar 21, 2018·Chemical Reviews·Guangye ZhangHe Yan
Feb 13, 2020·Journal of the American Chemical Society·Kun YangXugang Guo
Nov 9, 2018·Journal of Chemical Theory and Computation·Alec S BowenJuan J de Pablo
Aug 11, 2017·ACS Applied Materials & Interfaces·Hua SunWei Huang
Jul 22, 2016·Journal of the American Chemical Society·Dong MengZhaohui Wang

❮ Previous
Next ❯

Methods Mentioned

BETA
electron paramagnetic resonance
X-ray
optical spectroscopy
AFM

Software Mentioned

COSMO
Finalgrid6
TIGHTSCF
GIWAXS

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.