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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
Effect on charge transfer and charge recombination by insertion of a naphthalene-based bridge in molecular dyads
Andrew C Benniston1, Sophie Clift, Jerry Hagon
1Molecular Photonics Laboratory, School of Chemistry, Newcastle University, Newcastle upon Tyne, UK. a.c.benniston@ncl.ac.uk
Abstract:
The photophysical properties of two related dyads based on a N,N-dimethylaniline donor coupled to a fully-alkylated boron dipyrromethene (Bodipy) acceptor are described. In one dyad, BD1, the donor unit is attached directly to the Bodipy group, whereas in the second dyad, BD2, a naphthalene spacer separates the two units. Cyclic voltammograms recorded for the two dyads in deoxygenated MeCN containing a background electrolyte are consistent with the reversible one-electron oxidation of the N,N-dimethylaniline group and the reversible one-electron reduction of the Bodipy nucleus. There is a reasonable driving force (ΔG(CT)) for photoinduced charge transfer from the N,N-dimethylaniline to the Bodipy segment in MeCN. The charge-transfer state is formed for BD1 extremely fast (1.5 ps), but decays over 140 ps to partially restore the ground state. On the other hand, the charge-transfer state for BD2 is formed more slowly, but it decays extremely rapidly. Charge recombination for both dyads leads to a partial triplet formation on the Bodipy group. The naphthalene spacer group is extremely efficient at promoting back electron transfer.
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