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Title: Charge Separation Mechanisms in Ordered Films of Self-Assembled Donor–Acceptor Dyad Ribbons

Abstract

Orthogonal attachment of polar and nonpolar side-chains to a zinc porphyrin-perylenediimide dyad (ZnP-PDI, 1a) is shown herein to result in self-assembly of ordered supramolecular ribbons in which the ZnP and PDI molecules form segregated $$π$$-stacked columns. Following photoexcitation of the ordered ribbons, ZnP+•-PDI–• radical ion pairs form in <200 fs and subsequently produce a 30 ± 3% yield of free charge carriers that live for about 100 μs. Elongating the side chains on ZnP and PDI in 1b enhances the order of the films, but does not result in an increase in free charge carrier yield. In addition, this yield is independent of temperature, free energy of reaction, and the ZnP-PDI distance in the covalent dyad. These results suggest that the free charge carrier yield in this system is not limited by a bound charge transfer (CT) state or promoted by a vibronically hot CT state. Instead, it is likely that π-stacking of the segregated donors and acceptors within the ribbons results in delocalization of the charges following photoexcitation, allowing them to overcome Coulombic attraction and generate free charge carriers.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [1]
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  1. Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; National Science Foundation (NSF)
OSTI Identifier:
1399126
Grant/Contract Number:  
FG02-99ER14999; DGE-1324585
Resource Type:
Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 9; Journal Issue: 39; Journal ID: ISSN 1944-8244
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
ENGLISH
Subject:
36 MATERIALS SCIENCE; organic photovoltaics; femtosecond transient absorption spectroscopy; EPR; GIWAXS; self-assembly; thin films; charge transport

Citation Formats

Logsdon, Jenna L., Hartnett, Patrick E., Nelson, Jordan N., Harris, Michelle A., Marks, Tobin J., and Wasielewski, Michael R. Charge Separation Mechanisms in Ordered Films of Self-Assembled Donor–Acceptor Dyad Ribbons. United States: N. p., 2017. Web. doi:10.1021/acsami.7b02585.
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Logsdon, Jenna L., Hartnett, Patrick E., Nelson, Jordan N., Harris, Michelle A., Marks, Tobin J., & Wasielewski, Michael R. Charge Separation Mechanisms in Ordered Films of Self-Assembled Donor–Acceptor Dyad Ribbons. United States. https://doi.org/10.1021/acsami.7b02585
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Logsdon, Jenna L., Hartnett, Patrick E., Nelson, Jordan N., Harris, Michelle A., Marks, Tobin J., and Wasielewski, Michael R. Fri . "Charge Separation Mechanisms in Ordered Films of Self-Assembled Donor–Acceptor Dyad Ribbons". United States. https://doi.org/10.1021/acsami.7b02585. https://www.osti.gov/servlets/purl/1399126.
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@article{osti_1399126,
title = {Charge Separation Mechanisms in Ordered Films of Self-Assembled Donor–Acceptor Dyad Ribbons},
author = {Logsdon, Jenna L. and Hartnett, Patrick E. and Nelson, Jordan N. and Harris, Michelle A. and Marks, Tobin J. and Wasielewski, Michael R.},
abstractNote = {Orthogonal attachment of polar and nonpolar side-chains to a zinc porphyrin-perylenediimide dyad (ZnP-PDI, 1a) is shown herein to result in self-assembly of ordered supramolecular ribbons in which the ZnP and PDI molecules form segregated $π$-stacked columns. Following photoexcitation of the ordered ribbons, ZnP+•-PDI–• radical ion pairs form in <200 fs and subsequently produce a 30 ± 3% yield of free charge carriers that live for about 100 μs. Elongating the side chains on ZnP and PDI in 1b enhances the order of the films, but does not result in an increase in free charge carrier yield. In addition, this yield is independent of temperature, free energy of reaction, and the ZnP-PDI distance in the covalent dyad. These results suggest that the free charge carrier yield in this system is not limited by a bound charge transfer (CT) state or promoted by a vibronically hot CT state. Instead, it is likely that π-stacking of the segregated donors and acceptors within the ribbons results in delocalization of the charges following photoexcitation, allowing them to overcome Coulombic attraction and generate free charge carriers.},
doi = {10.1021/acsami.7b02585},
journal = {ACS Applied Materials and Interfaces},
number = 39,
volume = 9,
place = {United States},
year = {Fri Apr 21 00:00:00 EDT 2017},
month = {Fri Apr 21 00:00:00 EDT 2017}
}
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https://doi.org/10.1021/acsami.7b02585
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Cited by: 16 works
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Figures / Tables:

Figure 1 Figure 1: Charge separation (CS) mechanisms in OPVs: (1) through a vibronically cooled singlet CT state that can subsequently intersystem cross to a triplet CT; (2) through a “hot” singlet CT state; (3) directly to the CS state through delocalized bandlike states.
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