Benzo- and Naphthopentalenes: Syntheses, Structures, and Properties

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 carb...

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Published inJournal of organic chemistry Vol. 81; no. 17; pp. 7700 - 7710
Main Authors Kato, Shin-ichiro, Kuwako, Satoshi, Takahashi, Nobutaka, Kijima, Tomokazu, Nakamura, Yosuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHEMICAL-SHIFTS NICS
PENTALENE DERIVATIVES
AROMATICITY
DIBENZOPENTALENES
CYCLOOCTATETRAENE
ANNULATION
CASCADE CARBOPALLADATION REACTION
PYROLYSIS
ALKYNES
PHENYL
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Summary: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 8π 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 π-conjugation sufficiently.
Bibliography:KAKEN
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b01409