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Controlling Singlet Fission with Coordination Chemistry-Induced Assembly of Dipyridyl Pyrrole Bipentacenes

Ribson, Ryan D. and Choi, Gyeongshin and Hadt, Ryan G. and Agapie, Theodor (2020) Controlling Singlet Fission with Coordination Chemistry-Induced Assembly of Dipyridyl Pyrrole Bipentacenes. ACS Central Science, 6 (11). pp. 2088-2096. ISSN 2374-7943. https://resolver.caltech.edu/CaltechAUTHORS:20200728-104820571

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Abstract

Singlet fission has the potential to surpass current efficiency limits in next-generation photovoltaics and to find use in quantum information science. Despite the demonstration of singlet fission in various materials, there is still a great need for fundamental design principles that allow for tuning of photophysical parameters, including the rate of fission and triplet lifetimes. Here, we describe the synthesis and photophysical characterization of a novel bipentacene dipyridyl pyrrole (HDPP-Pent) and its Li- and K-coordinated derivatives. HDPP-Pent undergoes singlet fission at roughly 50% efficiency (τ_(SF) = 730 ps), whereas coordination in the Li complex induces significant structural changes to generate a dimer, resulting in a 7-fold rate increase (τ_(SF) = 100 ps) and more efficient singlet fission with virtually no sacrifice in triplet lifetime. We thus illustrate novel design principles to produce favorable singlet fission properties, wherein through-space control can be achieved via coordination chemistry-induced multipentacene assembly.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acscentsci.0c01044DOIArticle
https://doi.org/10.26434/chemrxiv.12712106.v1DOIDiscussion Paper
ORCID:
AuthorORCID
Hadt, Ryan G.0000-0001-6026-1358
Agapie, Theodor0000-0002-9692-7614
Additional Information:© 2020 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: August 5, 2020; Published: November 10, 2020. The authors thank Dr. Jay Winkler for assistance with time-resolved luminescence measurements, the Beckman Institute Laser Resource Center (BILRC) for access to the associated equipment, and Dr. David VanderVelde for NMR support and helpful discussions. Mike Takase and Larry Henling are acknowledged for crystallographic assistance. T.A. is grateful for the support provided by King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, offered under the KFUPM-Caltech Research Collaboration and the Joint Center for Artificial Photosynthesis, a DOE Energy Innovation Hub, supported through the Office of Science of the U.S. Department of Energy under Award DE-SC0004993. Financial support from Caltech and the Dow Next Generation Educator Fund is gratefully acknowledged (R.G.H.). The authors declare no competing financial interest.
Group:JCAP
Funders:
Funding AgencyGrant Number
King Fahd University of Petroleum and Minerals (KFUPM)UNSPECIFIED
Department of Energy (DOE)DE-SC0004993
CaltechUNSPECIFIED
Dow Next Generation Educator FundUNSPECIFIED
Subject Keywords:Nuclear fission, Hydrocarbons, Absorption, Fluorescence, Aromatic compounds
Issue or Number:11
Record Number:CaltechAUTHORS:20200728-104820571
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200728-104820571
Official Citation:Controlling Singlet Fission with Coordination Chemistry-Induced Assembly of Dipyridyl Pyrrole Bipentacenes. Ryan D. Ribson, Gyeongshin Choi, Ryan G. Hadt, and Theodor Agapie. ACS Central Science 2020 6 (11), 2088-2096; DOI: 10.1021/acscentsci.0c01044
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:104604
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:28 Jul 2020 19:02
Last Modified:25 Nov 2020 18:05

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