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Updated: May 30, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Colorimetric Detection of Naphthalene Enabled by Intra- to Intermolecular Charge Transfer Interplay Induced by
Kazushi Nakada1, Gary James Richards1, Akiko Hori1
1Graduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama-shi, Saitama, 337-8570, Japan.
Abstract:
A new Donor-Acceptor type pyrazinacene derivative (1) featuring strong ICT was synthesized by linking electron-donating triphenylamine (TPA) and electron-accepting CN groups via a pyrazinacene core. The compound exhibits a dramatic color change from greenish blue to red-violet upon selective recognition of naphthalene (3) to form a 1:1 co-crystal (1•3). This color change is induced by intermolecular CT between pyrazinacene and naphthalene's aromatic moieties, driven by π-hole⋅⋅⋅π interactions. Crystal structure analysis and DFT calculations confirm that the molecular recognition process is facilitated by the unique π-hole⋅⋅⋅π interactions, leading to a reversible color switching mechanism. The findings offer new insights into selective molecular recognition and ICT-CT interplay in nonporous adaptive crystals.
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