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Title: 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission

Journal Article · · Topics in Current Chemistry Collections
ORCiD logo [1]; ORCiD logo [2]
  1. National Renewable Energy Lab. (NREL), Golden, CO (United States)
  2. Univ. of Colorado, Boulder, CO (United States); Academy of Sciences of the Czech Republic, Prague (Czech Republic)
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In this review we first provide an introductory description of the singlet fission phenomenon and then describe the ground and electronically excited states of the parent 1,3-diphenylisobenzofuran chromophore (1) and about a dozen of its derivatives. A discussion of singlet fission in thin polycrystalline layers of these materials follows. The highest quantum yield of triplet formation by singlet fission, 200% at 80 K, is found in one of the two known crystal modification of the parent. In the other modification and in many derivatives, excimer formation competes successfully and triplet yields are low. A description of solution photophysics of covalent dimers is described in the next section. Triplet yields are very low, but interesting phenomena are uncovered. One is an observation of a separated-charges (charge-transfer) intermediate in highly polar solvents. The other is an observation of excitation isomerism in both singlet and triplet states, where in one isomer the excitation is delocalized over both halves of the covalent dimer, whereas in the other it is localized on one of the halves. In the last section we present the operation of a simple device illustrating the use of triplets generated by singlet fission for charge separation.

Research Organization:
Univ. of Colorado, Boulder, CO (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0007004
OSTI ID:
1678685
Journal Information:
Topics in Current Chemistry Collections, Vol. 2017; Related Information: Physical Organic Chemistry of Quinodimethanes - book title; ISSN 2367-4067
Publisher:
Springer NatureCopyright Statement
Country of Publication:
United States
Language:
English

Cited By (5)

Diabatization by Localization in the Framework of Configuration Interaction Based on Floating Occupation Molecular Orbitals (FOMO−CI) journal May 2019
Theoretical Studies of Singlet Fission: Searching for Materials and Exploring Mechanisms journal February 2018
Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission journal October 2018
Design of singlet fission chromophores with cyclic (alkyl)(amino) carbene building blocks journal June 2019
Feinabstimmung von intramolekularem resonantem Förster-Energietransfer und Aktivierung intramolekularer Singulettspaltung journal October 2018

Figures / Tables (21)

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
1
3-Diphenylisobenzofuran
Photophysics
Solar energy
Singlet fission
Covalent dimers