Abstract
Singlet exciton fission (SF) is a promising strategy for increasing photovoltaic efficiency, but in order for SF to be useful in solar cells, it should take place in a chromophore that is air-stable, highly absorptive, solution processable, and inexpensive. Unlike many SF chromophores, diketopyrrolopyrrole (DPP) conforms to these criteria, and here we investigate SF in DPP for the first time. SF yields in thin films of DPP derivatives, which are widely used in organic electronics and photovoltaics, are shown to depend critically on crystal morphology. Time-resolved spectroscopy of three DPP derivatives with phenyl (3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, PhDPP), thienyl (3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, TDPP), and phenylthienyl (3,6-di(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, PhTDPP) aromatic substituents in 100-200 nm thin films reveals that efficient SF occurs only in TDPP and PhTDPP (τSF = 220 ± 20 ps), despite the fact that SF is most exoergic in PhDPP. This result correlates well with the greater degree of π-overlap and closer π-stacking in TDPP (3.50 Å) and PhTDPP (3.59 Å) relative to PhDPP (3.90 Å) and demonstrates that SF in DPP is highly sensitive to the elec...Continue Reading
References
Sep 15, 2006·The Journal of Physical Chemistry. a·Mutasem Omar Sinnokrot, C David Sherrill
Dec 21, 2006·Journal of the American Chemical Society·Irina PaciJosef Michl
Dec 29, 2006·Organic Letters·Takashi KuboKazuhiro Nakasuji
Mar 14, 2008·The Journal of Physical Chemistry. a·Tanya N Singh-Rachford, Felix N Castellano
Dec 18, 2008·Physical Chemistry Chemical Physics : PCCP·Miroslav DvorákJörg Schroeder
Nov 6, 2009·Journal of the American Chemical Society·Johan C BijleveldRené A J Janssen
Dec 23, 2009·The Journal of Physical Chemistry. a·Andrew F SchwerinJosef Michl
Jun 10, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Bram P KarstenRené A J Janssen
Jul 24, 2010·Nature Chemistry·Paul M ZimmermanCharles B Musgrave
Aug 12, 2010·Journal of the American Chemical Society·Akihito KonishiTakashi Kubo
Aug 25, 2010·Advanced Materials·Johan C BijleveldRené A J Janssen
Sep 23, 2010·Journal of the American Chemical Society·Chen Wang, Michael J Tauber
Oct 15, 2010·Advanced Materials·Prashant SonarAnanth Dodabalapur
Nov 4, 2010·Journal of the American Chemical Society·Justin C JohnsonJosef Michl
Nov 9, 2010·Chemical Reviews·Millicent B Smith, Josef Michl
Feb 22, 2011·Journal of the American Chemical Society·Hugo BronsteinIain McCulloch
May 7, 2011·Journal of the American Chemical Society·Stephen LoserTobin J Marks
Jul 8, 2011·Chemical Communications : Chem Comm·Guillaume GoubertP H McBreen
Jan 20, 2012·Nano Letters·Bruno EhrlerNeil C Greenham
Feb 23, 2012·Journal of the American Chemical Society·Yali QiaoDaoben Zhu
Jul 5, 2012·The Journal of Physical Chemistry. a·Mindaugas KirkusStefan C J Meskers
Jul 24, 2012·Chemical Communications : Chem Comm·Stephen LoserTobin J Marks
Aug 23, 2012·Nature Communications·Bruno EhrlerNeil C Greenham
Sep 13, 2012·Advanced Materials·Priya J JadhavMarc A Baldo
Oct 20, 2012·Scientific Reports·Jun LiBeng S Ong
Dec 25, 2012·Physical Chemistry Chemical Physics : PCCP·C Pfaffenhuber, J Maier
Jan 10, 2013·Annual Review of Physical Chemistry·Millicent B Smith, Josef Michl
Apr 20, 2013·Science·Daniel N CongreveMarc A Baldo
Apr 25, 2013·Accounts of Chemical Research·Jiye LeeMarc A Baldo
Jun 27, 2013·Journal of the American Chemical Society·Nicholas E JacksonMark A Ratner
Sep 10, 2013·Journal of the American Chemical Society·Samuel W EatonMichael R Wasielewski
Dec 10, 2013·Annual Review of Physical Chemistry·Christopher J Bardeen
Oct 2, 2014·Physical Chemistry Chemical Physics : PCCP·Eric A MarguliesMichael R Wasielewski
Jan 13, 2015·Nature Materials·Erik BusbyMatthew Y Sfeir
Mar 19, 2015·Physical Chemistry Chemical Physics : PCCP·Ivana MatanovicPlamen Atanassov
Apr 4, 2013·The Journal of Physical Chemistry Letters·Nicolas RenaudMark A Ratner
Jan 1, 2015·Chemical Science·Patrick E HartnettMichael R Wasielewski
Citations
May 12, 2016·Journal of the American Chemical Society·You-Dan ZhangHao-Li Zhang
Jun 14, 2016·The Journal of Physical Chemistry. a·Jasper D CookNiels H Damrauer
Aug 23, 2016·Journal of the American Chemical Society·Catherine M MauckMichael R Wasielewski
Dec 16, 2016·Journal of the American Chemical Society·Eric A MarguliesMichael R Wasielewski
Dec 28, 2016·Journal of the American Chemical Society·Patrick E HartnettMichael R Wasielewski
Jan 24, 2017·The Journal of Physical Chemistry Letters·Tushita MukhopadhyaySatish Patil
May 19, 2017·Nature Communications·Bettina S BaselDirk M Guldi
May 20, 2017·Journal of the American Chemical Society·Zhijia WangMustafa Hayvali
Jan 13, 2018·Chemistry : a European Journal·Constantin HetzerRik R Tykwinski
Aug 30, 2018·Physical Chemistry Chemical Physics : PCCP·Li ShenXiyou Li
Aug 10, 2018·Chemical Science·Ryan D PensackGregory D Scholes
Jan 18, 2019·Nature·Benjamin D RavetzLuis M Campos
Nov 16, 2019·Nanoscale·Diana-Paola MedinaTomás Torres
Apr 25, 2019·Chemical Science·Bettina Sabine BaselRik R Tykwinski
Mar 25, 2020·Chemical Science·Bettina S BaselDirk M Guldi
Nov 23, 2016·Nature Chemistry·Eric A MarguliesMichael R Wasielewski
Aug 3, 2019·The Journal of Chemical Physics·Youn Jue BaeMichael R Wasielewski
Dec 18, 2020·ChemPlusChem·David RaisJosef Michl
Jan 27, 2021·Chemical Society Reviews·Tobias UllrichDirk M Guldi
Mar 23, 2021·Nature Communications·Peter J BuddenRichard H Friend
Apr 23, 2021·Physical Chemistry Chemical Physics : PCCP·Siobhan J BradleyKenneth P Ghiggino
Jun 30, 2021·Nanoscale·Ilias PapadopoulosDirk M Guldi
Jul 2, 2021·Chemical Science·Jordan ShaikhTracey M Clarke
Jul 29, 2021·The Journal of Physical Chemistry Letters·Maria Fumanal, Clémence Corminboeuf
Jul 15, 2021·Angewandte Chemie·Faizal KhanFrancis D'Souza
Nov 8, 2017·The Journal of Physical Chemistry Letters·Christopher GriecoJohn B Asbury
Aug 9, 2021·The Journal of Chemical Physics·A ManianS P Russo
Nov 4, 2020·The Journal of Physical Chemistry. a·Kaia R ParentiLuis M Campos
Jun 28, 2018·Journal of the American Chemical Society·Michelle ChenMichael R Wasielewski
Dec 15, 2017·Journal of the American Chemical Society·Aaron K LeSean T Roberts
Apr 13, 2018·Chemical Reviews·David Casanova
Sep 12, 2019·Journal of the American Chemical Society·Alexandr ZaykovJosef Michl
Dec 15, 2016·Journal of the American Chemical Society·Christopher GriecoJohn B Asbury
Oct 30, 2018·Journal of the American Chemical Society·Youn Jue BaeMichael R Wasielewski
Feb 23, 2019·Journal of the American Chemical Society·Andrew B PunDaniel N Congreve
Jun 17, 2020·ACS Nano·Arjun MenonDirk M Guldi
Nov 28, 2020·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Bart W H SaesRené A J Janssen
Jun 6, 2020·The Journal of Physical Chemistry. a·Li ShenXiyou Li
Nov 23, 2017·Journal of the American Chemical Society·Steven LukmanAndrew J Musser
Oct 7, 2020·Journal of the American Chemical Society·Carolyn E RamirezMichael R Wasielewski
Oct 13, 2020·Journal of the American Chemical Society·Long WangHongbing Fu
Nov 12, 2020·Journal of the American Chemical Society·Kealan J FallonLuis M Campos
May 18, 2018·ACS Applied Materials & Interfaces·Alec PickettSuchismita Guha
May 3, 2019·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Robin E M WillemsRené A J Janssen
Sep 26, 2020·The Journal of Physical Chemistry. a·Youn Jue BaeMichael R Wasielewski
Sep 9, 2019··Yi-Lin WuJordan Nelson