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Title: Striking the right balance of intermolecular coupling for high-efficiency singlet fission

Abstract

Singlet fission is a process that splits collective excitations, or excitons, into two with unity efficiency. This exciton splitting process, unique to molecular photophysics, has the potential to considerably improve the efficiency of optoelectronic devices through more efficient light harvesting. While the first step of singlet fission has been characterized in great detail, subsequent steps critical to achieving overall highly-efficient singlet-to-triplet conversion are only just beginning to become well understood. One of the most elementary suggestions, which has yet to be tested, is that an appropriately balanced coupling is necessary to ensure overall highly efficient singlet fission; that is, the coupling needs to be strong enough so that the first step is fast and efficient, yet weak enough to ensure the independent behavior of the resultant triplets. In this work, we show how high overall singlet-to-triplet conversion efficiencies can be achieved in singlet fission by ensuring that the triplets comprising the triplet pair behave as independently as possible. We show that side chain sterics govern local packing in amorphous pentacene derivative nanoparticles, and that this in turn controls both the rate at which triplet pairs form and the rate at which they decay. We show how compact side chains andmore » stronger couplings promote a triplet pair that effectively couples to the ground state, whereas bulkier side chains promote a triplet pair that appears more like two independent and long-lived triplet excitations. Our results show that the triplet pair is not emissive, that its decay is best viewed as internal conversion rather than triplet–triplet annihilation, and perhaps most critically that, in contrast to a number of recent suggestions, the triplets comprising the initially formed triplet pair cannot be considered independently. This work represents a significant step toward better understanding intermediates in singlet fission, and how molecular packing and couplings govern overall triplet yields.« less

Authors:
 [1];  [2];  [3];  [4];  [1]; ORCiD logo [5];  [1];  [1];  [3];  [3]; ORCiD logo [6]; ORCiD logo [7];  [5]; ORCiD logo [1]
  1. Department of Chemistry, Princeton University, Princeton, USA
  2. Department of Chemistry, University of Toronto, Toronto, Canada
  3. Department of Chemistry, The Pennsylvania State University, University Park, USA
  4. Department of Chemical and Biological Engineering, Princeton University, Princeton, USA
  5. Department of Chemistry, University of Kentucky, Lexington, USA
  6. Department of Chemical and Biological Engineering, Princeton University, Princeton, USA, Andlinger Center for Energy and the Environment
  7. Department of Chemistry, University of Toronto, Toronto, Canada, Department of Chemical Engineering and Applied Chemistry
Publication Date:
Research Org.:
Pennsylvania State Univ., University Park, PA (United States); Princeton Univ., NJ (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1441231
Alternate Identifier(s):
OSTI ID: 1505223
Grant/Contract Number:  
SC0008120; SC0015429
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 9 Journal Issue: 29; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Pensack, Ryan D., Tilley, Andrew J., Grieco, Christopher, Purdum, Geoffrey E., Ostroumov, Evgeny E., Granger, Devin B., Oblinsky, Daniel G., Dean, Jacob C., Doucette, Grayson S., Asbury, John B., Loo, Yueh-Lin, Seferos, Dwight S., Anthony, John E., and Scholes, Gregory D. Striking the right balance of intermolecular coupling for high-efficiency singlet fission. United Kingdom: N. p., 2018. Web. doi:10.1039/C8SC00293B.
Pensack, Ryan D., Tilley, Andrew J., Grieco, Christopher, Purdum, Geoffrey E., Ostroumov, Evgeny E., Granger, Devin B., Oblinsky, Daniel G., Dean, Jacob C., Doucette, Grayson S., Asbury, John B., Loo, Yueh-Lin, Seferos, Dwight S., Anthony, John E., & Scholes, Gregory D. Striking the right balance of intermolecular coupling for high-efficiency singlet fission. United Kingdom. doi:10.1039/C8SC00293B.
Pensack, Ryan D., Tilley, Andrew J., Grieco, Christopher, Purdum, Geoffrey E., Ostroumov, Evgeny E., Granger, Devin B., Oblinsky, Daniel G., Dean, Jacob C., Doucette, Grayson S., Asbury, John B., Loo, Yueh-Lin, Seferos, Dwight S., Anthony, John E., and Scholes, Gregory D. Mon . "Striking the right balance of intermolecular coupling for high-efficiency singlet fission". United Kingdom. doi:10.1039/C8SC00293B.
@article{osti_1441231,
title = {Striking the right balance of intermolecular coupling for high-efficiency singlet fission},
author = {Pensack, Ryan D. and Tilley, Andrew J. and Grieco, Christopher and Purdum, Geoffrey E. and Ostroumov, Evgeny E. and Granger, Devin B. and Oblinsky, Daniel G. and Dean, Jacob C. and Doucette, Grayson S. and Asbury, John B. and Loo, Yueh-Lin and Seferos, Dwight S. and Anthony, John E. and Scholes, Gregory D.},
abstractNote = {Singlet fission is a process that splits collective excitations, or excitons, into two with unity efficiency. This exciton splitting process, unique to molecular photophysics, has the potential to considerably improve the efficiency of optoelectronic devices through more efficient light harvesting. While the first step of singlet fission has been characterized in great detail, subsequent steps critical to achieving overall highly-efficient singlet-to-triplet conversion are only just beginning to become well understood. One of the most elementary suggestions, which has yet to be tested, is that an appropriately balanced coupling is necessary to ensure overall highly efficient singlet fission; that is, the coupling needs to be strong enough so that the first step is fast and efficient, yet weak enough to ensure the independent behavior of the resultant triplets. In this work, we show how high overall singlet-to-triplet conversion efficiencies can be achieved in singlet fission by ensuring that the triplets comprising the triplet pair behave as independently as possible. We show that side chain sterics govern local packing in amorphous pentacene derivative nanoparticles, and that this in turn controls both the rate at which triplet pairs form and the rate at which they decay. We show how compact side chains and stronger couplings promote a triplet pair that effectively couples to the ground state, whereas bulkier side chains promote a triplet pair that appears more like two independent and long-lived triplet excitations. Our results show that the triplet pair is not emissive, that its decay is best viewed as internal conversion rather than triplet–triplet annihilation, and perhaps most critically that, in contrast to a number of recent suggestions, the triplets comprising the initially formed triplet pair cannot be considered independently. This work represents a significant step toward better understanding intermediates in singlet fission, and how molecular packing and couplings govern overall triplet yields.},
doi = {10.1039/C8SC00293B},
journal = {Chemical Science},
number = 29,
volume = 9,
place = {United Kingdom},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
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DOI: 10.1039/C8SC00293B

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Cited by: 12 works
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Figures / Tables:

Figure 1 Figure 1: Chemical structures of the pentacene derivatives studied in this work arranged in order of increasing side chain bulkiness.

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    Works referencing / citing this record:

    Enhancing the intermolecular singlet fission efficiency by controlling the self-assembly of amphipathic tetracene derivatives in aqueous solution
    journal, January 2019

    • Tang, Zhaofeng; Zhou, Sainan; Wang, Xiangyang
    • Journal of Materials Chemistry C, Vol. 7, Issue 36
    • DOI: 10.1039/c9tc04070f

    Enhancing the intermolecular singlet fission efficiency by controlling the self-assembly of amphipathic tetracene derivatives in aqueous solution
    journal, January 2019

    • Tang, Zhaofeng; Zhou, Sainan; Wang, Xiangyang
    • Journal of Materials Chemistry C, Vol. 7, Issue 36
    • DOI: 10.1039/c9tc04070f