2017 Volume 90 Issue 12 Pages 1375-1381
In this study, a benzene-fused bis(thiaporphyrin) was synthesized by the retro-Diels–Alder reaction of a bicyclo[2.2.2]octadiene (BCOD)-fused bis(thiaporphyrin) precursor. This precursor was prepared by the double [3+1] porphyrin synthesis of the BCOD-fused dipyrrole with thiatripyrrane. The ultraviolet–visible (UV–vis) spectrum of benzene-fused bis(thiaporphyrin) in dichloromethane was extremely different from that of the corresponding benzene-fused bis(porphyrin). In contrast, extremely similar spectra were obtained in the presence of trifluoroacetic acid. The similar electronic structures in the protonated states were supported by X-ray analysis and time-dependent density-functional theory (TD-DFT) calculations.
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