Journal
JOURNAL OF PHYSICAL CHEMISTRY B
Volume 119, Issue 24, Pages 7644-7650Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp511704r
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Funding
- Center for Re-Defining Photovoltaic Efficiency Through Molecular-Scale Control, an Energy Frontier Research Center - U.S. Department of Energy (DOE), Office of Science, Office of Basic Energy Sciences [DE- SC0001085]
- 3M Non-Tenured Faculty Award
- NSF CAREER [DMR-1351293]
- U.S. Department of Energy, Basic Energy Sciences, Materials Sciences [DE-AC02-98CH10886]
- ASTAR Fellowship
- U.S. Department of Energy, Office of Basic Energy Sciences [DE-AC02-98CH10886]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1351293] Funding Source: National Science Foundation
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A common synthetic strategy used to design low-bandgap organic semiconductors employs the use of push-pull building blocks, where electron -rich and electron-deficient monomers are alternated along the pi-conjugated backbone of a molecule or polymer. Incorporating strong pull units with high electron affinity is a means to further decrease the optical gap for infrared optoelectronics or to develop n-type semiconducting materials. Here we show that the use of thiophene-1,1-dioxide as a strong acceptor in push-pull oligomers affects the electronic structure and carrier dynamics in unexpected ways. Critically, the overall excited-state lifetime is reduced by several orders of magnitude relative to unpxodized analogs due to the introduction of low-energy optically dark states and low-energy triplet states that allow for fast internal conversion and intramolecular singlet fission. We found that the electronic structure and excited-state lifetime are strongly dependent on the number of sequential thiophene-1,1-dioxide units. These results suggest that both the static and dynamical optical properties are highly tunable via small changes in chemical structure that have drastic effects on the optoelectronic properties, which can impact the types of applications that involve these materials.
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