Enantiopure 2-(2-ethylhexyl)dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes: synthesis, single-crystal structure and a surprising lack of influence of stereoisomerism on thin-film structure and electronic properties

Abstract

Starting from a chiral resolution of 2-ethylhexanoic acid followed by conversions of functional groups without interfering with the enantiopurity, we have successfully introduced an enantiopure 2-ethylhexyl group on to dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT) via a Negishi-coupling reaction to synthesize 2-(R)-(2-ethylhexyl)- and 2-(S)-(2-ethylhexyl)-DNTT (R- and S-EH-DNTT, respectively).