Synthesis and Properties of Quinoidal Fluorenofluorenes

被引：50
作者：
Barker, Joshua E.
Frederickson, Conerd K.
Jones, Michael H.
Zakharov, Lev N.
Haley, Michael M. [1 ]
机构：
[1] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 19期
基金：
美国国家科学基金会;
关键词：
SINGLET DIRADICALOIDS; ORGANIC ELECTRONICS; CHEMICAL-REACTIVITY; CHARACTER; AROMATICITY; HYDROCARBON; ANTIAROMATICITY; INDENOFLUORENES; SEMICONDUCTORS; STRATEGY;
D O I：
10.1021/acs.orglett.7b02605
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis and optoelectronic properties of 24 pi-electron, formally antiaromatic fluoreno[3,2-b]fluorene and fluoreno[4,3-c]fluorene (FF), are presented. The solid-state structure of [4,3-c]FF along with computationally analogous molecules shows that the outer rings are aromatic while the central four rings possess a bond-localized 2,6-naphthoquinodimethane motif. The antiaromaticity and biradical character of the FFs is assessed computationally, the results of which indicate the dominance of the closed-shell ground state for these molecules.
引用
收藏
页码：5312 / 5315
页数：4
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