2,3-Naphtho-Fused BODIPYs as Near-Infrared Absorbing Dyes

2,3-Naphtho-fused boron-dipyrromethenes (BODIPYs) 1a and 1b, which absorb near-infrared light at 740–770 nm with molar extinction coefficients above 105 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.2,3-并萘稠合硼二吡咯亚甲基（boron-dipyrromethenes, BODIPYs）1a与1b，可在四氢呋喃（THF）中吸收740~770 nm的近红外光，且摩尔消光系数高于10⁵ M⁻¹·cm⁻¹。本研究通过钯(II)催化的N-叔丁氧羰基（N-BOC）腙直接酰化反应，结合后续的Paal-Knorr吡咯合成法，完成了该类化合物的合成。对二苯并BODIPY进行简单的苯环稠合修饰，可使其吸收光谱发生显著红移。随后对1b进行分子内B,O环化反应得到化合物2，该化合物在830 nm处呈现出强吸收带。本研究通过理论计算与循环伏安法，对该系列化合物的结构-光学性能构效关系展开了系统探究。