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Updated: May 19, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Naphthoxaphospholes as examples of fluorescent phospha-acenes
Feng Li Laughlin1, Arnold L Rheingold, Nihal Deligonul
1Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA.
Abstract:
Seven new fluorescent 2-R-naphtho[2,3-d]oxaphospholes (R-NOPs) (4a–g; R = tBu (a), Ad (b), C(6)H(5) (c), 4-MeC(6)H(4) (d), 4-ClC(6)H(4) (e), 4-BrC(6)H(4) (f ), 4-MeOC(6)H(4) (g)), have been synthesized by cyclocondensation reactions of benzimidoyl chlorides with 3-phosphino-2-naphthol (3). The compounds were characterized by multinuclear NMR, UV-vis, and fluorescence spectroscopy. Compounds 4a–d and 4g were characterized by cyclic voltammetry experiments. The solid state structures of compounds 4b and 4d were also determined by single-crystal X-ray diffraction experiments.
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