Circularly Polarized Luminescence of Thiophene-Bridged Macrocyclic pseudo-meta [2.2]Paracyclophanes

Abstract

Chiral organic molecules possessing high quantum yields, circular dichroism, and circularly polarized luminescence values have great potential as optically active materials for future applications. Recently, the identification of a promising class of inherently chiral compounds was reported, namely macrocyclic 1,3-butadiyne-linked pseudo-meta[2.2]paracyclophanes, displaying high circular dichroism and related gabs values albeit modest quantum yields. Increasing the quantum yields in an attempt to get bright circularly polarized light emitters, the high-yielding heterocyclization of those 1,3-butadiyne bridges resulting in macrocyclic 2,5-thienyls-linked pseudo-meta [2.2]paracyclophanes is herein described. The chiroptical properties of both, the previously reported 1,3-butadiyne, and the novel 2,5-thienyl bridged macrocycles of various sizes, are experimentally recorded, and theoretically described using density-functional theory.