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
Jul 18, 2002·Journal of the American Chemical Society·Jovan M GiaimoMichael R Wasielewski
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
Jun 4, 2004·Journal of the American Chemical Society·Josemon JacobKlaus Müllen
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
Jun 21, 2007·Angewandte Chemie·Theo E KaiserFrank Würthner
Aug 19, 2007·Journal of the American Chemical Society·Hualei QianDaoben Zhu
Jan 4, 2008·The Journal of Physical Chemistry. a·Wenbo EMaxwell J Crossley
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
Apr 7, 2010·Chemical Communications : Chem Comm·Zhongyi YuanXuhong Qian
May 21, 2010·Physical Review Letters·Justin M HodgkissRichard H Friend
Jul 20, 2010·Advanced Materials·Yongye LiangLuping Yu
Nov 23, 2010·Advanced Materials·Jodi M SzarkoLin X Chen
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
Feb 1, 2012·Accounts of Chemical Research·Yongfang Li
Mar 1, 2012·Science·Artem A BakulinRichard H Friend
Apr 12, 2012·Chemical Communications : Chem Comm·Yuze LinXiaowei Zhan
Jun 22, 2013·Advanced Materials·Alexander SharenkoGuillermo C Bazan
Aug 9, 2013·Advanced Materials·Xin ZhangJiannian Yao
Dec 7, 2013·Chemical Communications : Chem Comm·Wei JiangZhaohui Wang
Jan 28, 2014·Journal of the American Chemical Society·Brett M SavoieMark A Ratner
Mar 8, 2014·Nature Communications·Kjell CnopsPaul Heremans
Apr 2, 2014·Advanced Materials·Jean RoncaliPhilippe Blanchard
Apr 30, 2014·Accounts of Chemical Research·Long YeJianhui Hou
May 21, 2014·Journal of the American Chemical Society·Yu ZhongColin Nuckolls
Jun 20, 2014·Advanced Materials·Yue ZangAlex K-Y Jen
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
Nov 11, 2014·Nature Communications·Yuhang LiuHe Yan
Nov 29, 2014·Advanced Materials·Yuhang LiuHe Yan
Apr 10, 2015·The Journal of Physical Chemistry. a·Samuel W EatonMichael R Wasielewski
Apr 29, 2015·ACS Applied Materials & Interfaces·Long YeJianhui Hou
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
Sep 19, 2015·Nature Communications·Yu ZhongColin Nuckolls
Citations
Dec 6, 2017·Advanced Materials·Nicholas D EasthamTobin J Marks
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
May 10, 2020·Materials·Keisuke FujimotoMasahiro Hiramoto
Dec 3, 2016·The Journal of Chemical Physics·Nicholas E JacksonMark A Ratner
Sep 21, 2018·Frontiers in Chemistry·Kaiwen LinYong Cao
Oct 21, 2017·Advanced Science·Yu XiongBeng S Ong
Mar 15, 2018·Physical Chemistry Chemical Physics : PCCP·Daiki KatoTaku Hasobe
Dec 3, 2016·Nature Communications·Haijun BinYongfang Li
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
Apr 3, 2019·Advanced Science·Zhenghui LuoChuluo Yang
Feb 19, 2019·Chemical Science·Margarita MiltonColin Nuckolls
Mar 21, 2017·Polymers·Tanwistha GhoshVijayakumar C Nair
Dec 20, 2018·Chemical Communications : Chem Comm·Ming HuYiwang Chen
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
May 4, 2017·Advanced Materials·Yikun GuoDahui Zhao
Dec 5, 2017·Advanced Science·Zhenzhen ZhangYingping Zou
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
Jul 22, 2017·Chemistry, an Asian Journal·Liang ZhaoWei Huang
Nov 20, 2020·Chemical Science·Ariel A LeonardLin X Chen
May 22, 2021·Physical Chemistry Chemical Physics : PCCP·Suryakanti DebataSridhar Sahu
May 20, 2021·Physical Chemistry Chemical Physics : PCCP·Tobias KochNikos L Doltsinis
Jun 1, 2021·Frontiers in Chemistry·Kaiwen LinYong Cao
Dec 20, 2019·Chemical Science·Feng SuTing-Bin Wen
Jun 11, 2021·ChemPlusChem·Tomoya Ogawa, Daiki Kuzuhara
Jun 24, 2021·Angewandte Chemie·Chunsheng CaiYongfang Li
Dec 28, 2016·Journal of the American Chemical Society·Patrick E HartnettMichael R Wasielewski
Sep 27, 2018·Organic Letters·Jiajun WuHui-Jun Zhang
Jul 28, 2018·ACS Applied Materials & Interfaces·Mingliang WuJianlong Xia
Apr 17, 2018·ACS Applied Materials & Interfaces·Yuli YinYong Zhang
Jan 23, 2019·ACS Applied Materials & Interfaces·Han HanDahui Zhao
Apr 22, 2017·ACS Applied Materials & Interfaces·Jenna L LogsdonMichael R Wasielewski
Dec 19, 2017·ACS Applied Materials & Interfaces·Zhitian LiuXiang Gao
May 11, 2017·The Journal of Organic Chemistry·Yu HuYiwang Chen
Sep 29, 2017·Organic Letters·Jiajun WuHui-Jun Zhang
Mar 21, 2018·Chemical Reviews·Guangye ZhangHe Yan
Dec 4, 2019·ACS Omega·Samya NaqviRachana Kumar
Nov 8, 2017·Journal of the American Chemical Society·Jianquan 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
Oct 26, 2016·Journal of the American Chemical Society·Yankang YangYongfang Li
Aug 11, 2017·ACS Applied Materials & Interfaces·Hua SunWei Huang
Jul 22, 2016·Journal of the American Chemical Society·Dong MengZhaohui Wang