Golden Age of Fluorenylidene Phosphaalkenes-Synthesis, Structures, and Optical Properties of Heteroaromatic Derivatives and Their Gold Complexes

J Org Chem. 2020 Nov 20;85(22):14619-14626. doi: 10.1021/acs.joc.0c01336. Epub 2020 Sep 4.

Abstract

The substitution of 2,7-dibromo-9-fluorenyl phosphaalkenes with heteroaromatic substituents (bithiophene, benzothiophene, pyridine) offers access to interesting push-pull dye molecules. Steric shielding due to the bulky P-substituent gives marked different reactivities at the 2- and 7-positions, allowing the synthesis of mixed/asymmetric derivatives. Further functionalization via gold(I) coordination was demonstrated and increased the acceptor character, concomitant with a red-shifted absorption.