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An Exploration of S...
An Exploration of Substituent Effects on the Photophysical Properties of Monobenzopentalenes
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- Gazdag, Tamás (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences,Eötvös Loránd University (ELTE)
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- Meiszter, Enikő (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences,Budapesti Muszaki es Gazdasagtudomanyi Egyetem,Budapest University of Technology and Economics
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- Mayer, Péter J. (author)
- Uppsala universitet,Uppsala University,Magyar Tudomanyos Akademia,Hungarian Academy of Sciences
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- Holczbauer, Tamás (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences
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- Ottosson, H. (author)
- Uppsala universitet,Uppsala University
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- Maurer, Andrew Brian, 1991 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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- Abrahamsson, Maria, 1975 (author)
- Chalmers tekniska högskola,Chalmers University of Technology
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- London, Gábor (author)
- Magyar Tudomanyos Akademia,Hungarian Academy of Sciences
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(creator_code:org_t)
- 2024
- 2024
- English.
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In: ChemPhysChem. - 1439-7641 .- 1439-4235. ; 25:7
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https://doi.org/10.1...
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Abstract
Subject headings
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- Monobenzopentalenes have received moderate attention compared to dibenzopentalenes, yet their accessibility as stable, non-symmetric structures with diverse substituents could be interesting for materials applications, including molecular photonics. Recently, monobenzopentalene was considered computationally as a potential chromophore for singlet fission (SF) photovoltaics. To advance this compound class towards photonics applications, the excited state energetics must be characterized, computationally and experimentally. In this report we synthesized a series of stable substituted monobenzopentalenes and provided the first experimental exploration of their photophysical properties. Structural and opto-electronic characterization revealed that all derivatives showed 1H NMR shifts in the olefinic region, bond length alternation in the pentalene unit, low-intensity absorptions reflecting the ground-state antiaromatic character and in turn the symmetry forbidden HOMO-to-LUMO transitions of ~2 eV and redox amphotericity. This was also supported by computed aromaticity indices (NICS, ACID, HOMA). Accordingly, substituents did not affect the fulfilment of the energetic criterion of SF, as the computed excited-state energy levels satisfied the required E(S1)/E(T1)>2 relationship. Further spectroscopic measurements revealed a concentration dependent quenching of the excited state and population of the S2 state on the nanosecond timescale, providing initial evidence for unusual photophysics and an alternative entry point for singlet fission with monobenzopentalenes.
Subject headings
- NATURVETENSKAP -- Kemi -- Fysikalisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Physical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- excited state
- singlet fission
- pentalene
- photophysics
- antiaromaticity
- substituent effects
Publication and Content Type
- art (subject category)
- ref (subject category)
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