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Substituent effects on energetics and crystal morphology modulate singlet fission in 9,10-bis(phenylethynyl)anthracenes
- Publication Year :
- 2019
- Publisher :
- American Institute of Physics (AIP), 2019.
-
Abstract
- Singlet fission (SF) converts a singlet exciton into two triplet excitons in two or more electronically coupled organic chromophores, which may then be used to increase solar cell efficiency. Many known SF chromophores are unsuitable for device applications due to chemical instability or low triplet state energies. The results described here show that efficient SF occurs in derivatives of 9,10-bis(phenylethynyl)anthracene (BPEA), which is a highly robust and tunable chromophore. Fluoro and methoxy substituents at the 4- and 4′-positions of the BPEA phenyl groups control the intermolecular packing in the crystal structure, which alters the interchromophore electronic coupling, while also changing the SF energetics. The lowest excited singlet state (S1) energy of 4,4′-difluoro-BPEA is higher than that of BPEA so that the increased thermodynamic favorability of SF results in a (16 ± 2 ps)−1 SF rate and a 180% ± 16% triplet yield, which is about an order of magnitude faster than BPEA with a comparable triplet yield. By contrast, 4-fluoro-4′-methoxy-BPEA and 4,4′-dimethoxy-BPEA have slower SF rates, (90 ± 20 ps)−1 and (120 ± 10 ps)−1, and lower triplet yields, (110 ± 4)% and (168 ± 7)%, respectively, than 4,4′-difluoro-BPEA. These differences are attributed to changes in the crystal structure controlling interchromophore electronic coupling as well as SF energetics in these polycrystalline solids.
- Subjects :
- Anthracene
010304 chemical physics
Intermolecular force
Substituent
General Physics and Astronomy
Crystal structure
Chromophore
010402 general chemistry
Photochemistry
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
chemistry
Yield (chemistry)
0103 physical sciences
Singlet fission
Physical and Theoretical Chemistry
Triplet state
Subjects
Details
- Language :
- English
- ISSN :
- 00219606
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....a2139d0e4103d855151c3aaac79ea6fc