Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines
Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines, S,N-doped pyrene analogs, were prepared by combination of Pd catalyzed cross-coupling reactions and acid-mediated cycloisomerization. The modular scope of the synthesis allowed for access to a variety of functionalized derivatives. The photophysical...
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| Veröffentlicht in: | Journal of organic chemistry 2023-07, Vol.88 (13), p.8802-8824 |
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| container_issue | 13 |
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| container_title | Journal of organic chemistry |
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| creator | Molenda, Ricardo Polkaehn, Jonas Argüello Cordero, Miguel Andre Villinger, Alexander Ehlers, Peter Lochbrunner, Stefan Langer, Peter |
| description | Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines, S,N-doped pyrene analogs, were prepared by combination of Pd catalyzed cross-coupling reactions and acid-mediated cycloisomerization. The modular scope of the synthesis allowed for access to a variety of functionalized derivatives. The photophysical properties have been studied in detail by steady-state and femtosecond transient absorption accompanied by cyclic voltammetry and (TD)-DFT calculations. The introduction of a five-membered thiophene into the 2-azapyrene scaffold leads to redshifted emission and substantial effects on the excited state dynamics, e.g., quantum yield, lifetime, decay rates, and the ISC ability, which can be further tuned by the substitution pattern of the heterocyclic scaffold. |
| doi_str_mv | 10.1021/acs.joc.3c00632 |
| format | Article |
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| source | ACS Publications |
| title | Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines |
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