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Title: Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells

Abstract

In this study, two analogous perylene diimide (PDI) trimers, whose structures show rotatable single bond π-bridge connection (twisted) vs. rigid/fused π-bridge connection (planar), were synthesized and investigated. We show via time resolved spectroscopic measurements how the π-bridge connections in A–π–D–π–A–π–D–π–A multichromophoric PDI systems strongly affect the triplet yield and triplet formation rate. In the planar compound, with stronger intramolecular charge transfer (ICT) character, triplet formation occurs via conventional intersystem crossing. However, clear evidence of efficient and fast intramolecular singlet exciton fission (iSEF) is observed in the twisted trimer compound with weaker ICT character. Multiexciton triplet generation and separation occur in the twisted (flexible-bridged) PDI trimer, where weak coupling among the units is observed as a result of the degenerate double triplet and quintet states, obtained by quantum chemical calculations. The high triplet yield and fast iSEF observed in the twisted compound are due not only to enthalpic viability but also to the significant entropic gain allowed by its trimeric structure. Our results represent a significant step forward in structure–property understanding, and may direct the design of new efficient iSEF materials.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3];  [4];  [2];  [2];  [4]; ORCiD logo [2]; ORCiD logo [2]
+ Show Author Affiliations
  1. Department of Chemistry, University of Michigan, Ann Arbor, USA, Department of Chemistry Biology and Biotechnology
  2. Department of Chemistry, University of Michigan, Ann Arbor, USA
  3. Department of Chemistry, University of Michigan, Ann Arbor, USA, Department of Chemistry
  4. Department of Chemistry, The James Franck Institute, The University of Chicago, Chicago, USA
Publication Date:
Research Org.:
Univ. of Michigan, Ann Arbor, MI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
OSTI Identifier:
1647278
Alternate Identifier(s):
OSTI ID: 1715513
Grant/Contract Number:  
SC0012482; DMR-1709005
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 11 Journal Issue: 33; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Carlotti, Benedetta, Madu, Ifeanyi K., Kim, Hyungjun, Cai, Zhengxu., Jiang, Hanjie, Muthike, Angelar K., Yu, Luping, Zimmerman, Paul M., and Goodson, Theodore. Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells. United Kingdom: N. p., 2020. Web. doi:10.1039/D0SC03271A.
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Carlotti, Benedetta, Madu, Ifeanyi K., Kim, Hyungjun, Cai, Zhengxu., Jiang, Hanjie, Muthike, Angelar K., Yu, Luping, Zimmerman, Paul M., & Goodson, Theodore. Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells. United Kingdom. https://doi.org/10.1039/D0SC03271A
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Carlotti, Benedetta, Madu, Ifeanyi K., Kim, Hyungjun, Cai, Zhengxu., Jiang, Hanjie, Muthike, Angelar K., Yu, Luping, Zimmerman, Paul M., and Goodson, Theodore. Wed . "Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells". United Kingdom. https://doi.org/10.1039/D0SC03271A.
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@article{osti_1647278,
title = {Activating intramolecular singlet exciton fission by altering π-bridge flexibility in perylene diimide trimers for organic solar cells},
author = {Carlotti, Benedetta and Madu, Ifeanyi K. and Kim, Hyungjun and Cai, Zhengxu. and Jiang, Hanjie and Muthike, Angelar K. and Yu, Luping and Zimmerman, Paul M. and Goodson, Theodore},
abstractNote = {In this study, two analogous perylene diimide (PDI) trimers, whose structures show rotatable single bond π-bridge connection (twisted) vs. rigid/fused π-bridge connection (planar), were synthesized and investigated. We show via time resolved spectroscopic measurements how the π-bridge connections in A–π–D–π–A–π–D–π–A multichromophoric PDI systems strongly affect the triplet yield and triplet formation rate. In the planar compound, with stronger intramolecular charge transfer (ICT) character, triplet formation occurs via conventional intersystem crossing. However, clear evidence of efficient and fast intramolecular singlet exciton fission (iSEF) is observed in the twisted trimer compound with weaker ICT character. Multiexciton triplet generation and separation occur in the twisted (flexible-bridged) PDI trimer, where weak coupling among the units is observed as a result of the degenerate double triplet and quintet states, obtained by quantum chemical calculations. The high triplet yield and fast iSEF observed in the twisted compound are due not only to enthalpic viability but also to the significant entropic gain allowed by its trimeric structure. Our results represent a significant step forward in structure–property understanding, and may direct the design of new efficient iSEF materials.},
doi = {10.1039/D0SC03271A},
journal = {Chemical Science},
number = 33,
volume = 11,
place = {United Kingdom},
year = {Wed Aug 26 00:00:00 EDT 2020},
month = {Wed Aug 26 00:00:00 EDT 2020}
}
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https://doi.org/10.1039/D0SC03271A
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