Open AccessModulating Paratropicity Strength in Diareno-Fused Antiaromatics
Author(s) -
Conerd K. Frederickson,
Lev N. Zakharov,
Michael M. Haley
Publication year - 2016
Publication title -
journal of the american chemical society
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.6b11397
Subject(s) - antiaromaticity , pentalene , cyclobutadiene , chemistry , fluorene , molecule , computational chemistry , regioselectivity , semiconductor , conjugated system , chemical physics , nanotechnology , aromaticity , organic chemistry , polymer , optoelectronics , physics , materials science , catalysis
Understanding and controlling the electronic structure of molecules is crucial when designing and optimizing new organic semiconductor materials. We report the regioselective synthesis of eight π-expanded diarenoindacene analogues based on the indeno[1,2-b]fluorene framework along with the computational investigation of an array of diareno-fused antiaromatic compounds possessing s-indacene, pentalene, or cyclobutadiene cores. Analysis of the experimental and computationally derived optoelectronic properties uncovered a linear correlation between the bond order of the fused arene bond and the paratropicity strength of the antiaromatic unit. The E red 1 for the pentalene and indacene core molecules correlates well with their calculated NICS πZZ values. The findings of this study can be used to predict the properties of, and thus rationally design, new diareno-fused antiaromatic molecules for use as organic semiconductors.