| Abstract: | ![]()
A near‐infrared (NIR) polymethine dye ( 1 ), consisting of a cyclohepta[1,2‐b ;4,3‐b′ ]dithiophene and two phenol moieties, was synthesized. This dye exhibited pH‐responsive changes in its photophysical properties due to a two‐step acid–base equilibrium that produced a protonated cation ( 1H+ ) and an anion ( 1− ). While 1H+ showed an intense fluorescence in the red region of the visible spectrum, 1− exhibited a strong absorption in the NIR region. The tropylium ion character in 1H+ induces high pK a1 and pK a2 values for 1 . Moreover, a stable radical ( 1. ) was prepared, which showed a NIR absorption band with a maximum at circa 1600 nm. The cyclic voltammogram of 1. revealed a two‐step reversible redox process that produced 1− and the cation 1+ , which is different from 1H+ . These redox processes accompany drastic electrochromic changes in the vis–NIR region. Overall, 1 is susceptible to multiple interconversions between five forms, due to the multifaceted character of the cycloheptadithiophene skeleton. |
