Kinetically stabilized 1,3-diarylisobenzofurans and the possibility of preparing large, persistent isoacenofurans with unusually small HOMO–LUMO gaps

• Qian Liu and
• Glen P. Miller

Beilstein J. Org. Chem. 2024, 20, 1099–1110, doi:10.3762/bjoc.20.97

• Qian Liu Glen P. Miller Department of Chemistry, University of New Hampshire, 23 Academic Way, Durham, New Hampshire 03864-3598, USA 10.3762/bjoc.20.97 Abstract DFT calculations demonstrate that an isoacenofuran of any size possesses a smaller HOMO–LUMO gap than the corresponding acene bearing an

• gaps is achievable. As such, these molecules deserve increased attention as potential p-type organic semiconductors. Keywords: acene; DFT calculation; highly delocalized π-system; isoacenofuran; isobenzofuran; kinetically stabilized; organic semiconductor; small HOMO–LUMO gap; synthesis; Introduction

• smaller HOMO–LUMO gaps. Isoacenofurans are composed of linearly annellated benzene rings that terminate with a furan ring. Isoacenofurans and acenes possess isoelectronic π-systems when the total number of rings is the same. Unlike acenes, none of the 6-membered rings in an isoacenofuran possess an