Benzo- and Naphthopentalenes: Syntheses, Structures, and Properties
Benzo- and Naphthopentalenes: Syntheses, Structures, and Properties
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DOI：
10.1021/acs.joc.6b01409
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发表时间：
2016-09-02
影响因子：
3.6
通讯作者：
Nakamura, Yosuke
中科院分区：
文献类型：
--
作者：
Kato, Shin-ichiro;Kuwako, Satoshi;Nakamura, Yosuke
合成了苯并和萘戊二烯衍生物，并从理论上和实验上考察了结构变化对其抗芳性和光电电化学性能的影响。结果表明，随着戊二烯与芳香族共享的碳-碳键（[5,6]结）键序的增加，戊二烯的8 π反芳香族特征增强，HOMO-LUMO间隙减小，同时伴随着HOMO能级的升高和LUMO能级的降低。在戊二烯骨架和苯基之间的乙烯基被证明充分扩展了偶联。
Benzo- and naphthopentalene derivatives were synthesized, and the effects of structural variations on their antiaromaticity and optoelectronic and electrochemical properties were examined experimentally and theoretically in detail. The results unveiled that with increasing the bond order of the carbon-carbon bond ([5,6] junction) shared by the pentalene and aromatic moieties, the 8 pi antiaromatic character of pentalene is enhanced and the HOMO-LUMO gap is decreased, which accompanies both the elevation of the HOMO level and the lowering of the LUMO level. The ethynylene units between the pentalene skeleton and the phenyl groups proved to extend pi-conjugation sufficiently.