BODIPY-Derived Photoremovable Protecting Groups Unmasked with Green Light

Pratik P. Goswami
Aleem Ayed, Iowa State University
Christie L. Beck
Toshia R. Albright
Kaitlyn M. Mahoney
Ryan Unash
Emily A. Smith, Iowa State University
Arthur Winter, Iowa State University

Reprinted (adapted) with permission from Journal of the American Chemical Society, 137(11); 3783-3786. Doi: 10.1021/jacs.5b01297. Copyright 2015 American Chemical Society.

Abstract

Photoremovable protecting groups derived from meso-substituted BODIPY dyes release acetic acid with green wavelengths >500 nm. Photorelease is demonstrated in cultured S2 cells. The photocaging structures were identified by our previously proposed strategy of computationally searching for carbocations with low-energy diradical states as a possible indicator of a nearby productive conical intersection. The superior optical properties of these photocages make them promising alternatives