Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based π-Conjugated Molecules for Optoelectronics

Abstract

Controllable direct C-H arylation with high regioselectivity is highly desirable yet remains a formidable challenge. Herein, a facile regioselective direct C-H arylation is developed for efficient construction of a variety of symmetrical dithienophthalimide-based π-conjugated molecules. The resulting methodology is applicable to a wide range of substrates, from electron-rich units to electron-deficient units with large steric end groups. Aryl halides have been confirmed to be able to couple with dithienophthalimide (DTI) via direct C-H arylation, showing high regioselectivity. Varying the functional end groups onto the DTI core has been demonstrated to fine tune the emission colors to cover most of the visible spectra. The results suggest a facile strategy towards highly selective direct C-H arylation, opening the prospects towards efficient construction of π-conjugated molecules for various potential optoelectronic applications.