Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan.
Chem Commun (Camb). 2012 Jun 7;48(45):5671-3. doi: 10.1039/c2cc31546g. Epub 2012 May 1.
Although angular-shaped naphthodifurans, naphtho[1,2-b;5,6-b']- and naphtho[2,1-b;6,5-b']-difuran, are formally isoelectronic with chrysene as their thiophene counterparts, naphtho[1,2-b;5,6-b']- and naphtho[2,1-b;6,5-b']-dithiophene, the HOMO energy level of naphthodifurans is much higher than those of naphthodithiophenes and chrysene. The difference in electronic structure in the ground state can be explained by distinct electronic perturbation from the outermost aromatic rings.
尽管角状萘并[1,2-b;5,6-b']-和萘并[2,1-b;6,5-b']-二呋喃与噻吩类似物中的苝一样在形式上是等电子体，但萘并[1,2-b;5,6-b']-和萘并[2,1-b;6,5-b']-二噻吩的 HOMO 能级却远高于萘并二噻吩和苝。这种基态下电子结构的差异可以用最外层芳环的明显电子微扰来解释。
