Rapid Construction of Fold-Line-Shaped BN-Embedded Polycyclic Aromatic Compounds through Diels–Alder Reaction

The Diels–Alder reaction strategy that can rapidly extend the conjugated backbone was applied to facilely synthesize fold-line, coplanar BN-embedded polycyclic aromatic hydrocarbons from simple small BN compounds. The molecular structures and packing modes of these BN-embedded acenes were confirmed...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 1; pp. 241 - 247
Main Authors Zhang, Peng-Fei, Zhuang, Fang-Dong, Sun, Ze-Hao, Lu, Yang, Wang, Jie-Yu, Pei, Jian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.01.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
NAPHTHALENE
NARROW GRAPHENE NANORIBBONS
BISTETRACENE
OPTOELECTRONIC PROPERTIES
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Summary:The Diels–Alder reaction strategy that can rapidly extend the conjugated backbone was applied to facilely synthesize fold-line, coplanar BN-embedded polycyclic aromatic hydrocarbons from simple small BN compounds. The molecular structures and packing modes of these BN-embedded acenes were confirmed by single-crystal X-ray diffraction. Their electronic and photophysical properties were studied by using UV–vis, fluorescence spectroscopy, electrochemical cyclic voltammetry, and density functional theory calculations. These results demonstrate the efficiency and feasibility of this synthetic strategy.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02956