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Updated: Jul 27, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis and Properties of Thieno[2',3',4':4,5]naphtho[1,8-
Ricardo Molenda1, Jonas Polkaehn1, Miguel Andre Argüello Cordero2
1Institut für Chemie, Universität Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany.
Abstract:
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.
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