A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents.

ABSTRACT

While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a ß-carbonyl-based polar substituent. The results reveal a mechanism wherein the ß-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the ß-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the ß-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.