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2,3-Naphtho-Fused BODIPYs as Near-Infrared Absorbing Dyes
Sho Yamazawa1, Mika Nakashima1, Yukie Suda1
1Department of Applied Chemistry, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University , 1-1 Minami-Ohsawa, Hachioji, Tokyo 192-0397, Japan.
Abstract:
2,3-Naphtho-fused boron-dipyrromethenes (BODIPYs) 1a and 1b, which absorb near-infrared light at 740-770 nm with molar extinction coefficients above 10(5) M(-1) cm(-1) in THF, have been synthesized through a palladium(II)-catalyzed direct acylation of N-BOC hydrazones and subsequent Paal-Knorr pyrrole synthesis. Simple benzo-annulation of dibenzo-BODIPY caused a significant red-shift in the absorption. Subsequent intramolecular B,O-cyclization of 1b gave 2, which exhibited an intense absorption band at 830 nm. The structure-optical property relationship has been investigated using theoretical calculations and cyclic voltammetry.
