Azulene-Based BN-Heteroaromatics

被引：60
作者：
Xin, Hanshen [1 ]
Li, Jing [1 ]
Yang, Xiaodi [2 ]
Gao, Xike [1 ]
机构：
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Key Lab Synthet & Self Assembly Chem Organ Funct, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 01期
基金：
中国国家自然科学基金;
关键词：
CONJUGATED POLYMERS; BIAZULENE DIIMIDES; HETEROACENES; BLUE; TERAZULENE; STABILITY; OLIGOMERS; BEHAVIOR; UNIT;
D O I：
10.1021/acs.joc.9b01724
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Azulene, a nonalternant bicyclic aromatic hydrocarbon, has unique chemical and physical properties and is considered to be a promising building block for constructing novel polycyclic aromatic hydrocarbons (PAHs) and heteroaromatics. We present here the first two azulene-based BN-heteroaromatics Az-BN-1 and Az-BN-2. The chemical structures and optical and electrochemical properties of both compounds have been investigated, as well as their sensing behavior in response to fluoride ion. Az-BN-1 and Az-BN-2 show different photophysical properties from other reported BN-embedded PAHs, such as lower band gaps and unusual fluorescence. In addition, Az-BN-1 and Az-BN-2 exhibit unexpected deboronization upon addition of trifluoroacetic acid, which distinguishes them from other reported BN-heteroaromatics and can be ascribed to the unique property of the azulene unit.
引用
收藏
页码：70 / 78
页数：9
相关论文
共 51 条
[41]   Synthesis and Properties of C2h-Symmetric BN-Heteroacenes Tailored through Aromatic Central Cores [J].
Wang, Xinyang ;
Zhang, Fan ;
Gao, Jianhua ;
Fu, Yubin ;
Zhao, Wuxue ;
Tang, Ruizhi ;
Zhang, Wanzheng ;
Zhuang, Xiaodong ;
Feng, Xinliang .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) :10127-10133
[42]   Graphenes as potential material for electronics [J].
Wu, Jishan ;
Pisula, Wojciech ;
Muellen, Klaus .
CHEMICAL REVIEWS, 2007, 107 (03) :718-747
[43]   6,6′-Diaryl-substituted biazulene diimides for solution-processable high-performance n-type organic semiconductors [J].
Xin, Hanshen ;
Li, Jing ;
Ge, Congwu ;
Yang, Xiaodi ;
Xue, Tianrui ;
Gao, Xike .
MATERIALS CHEMISTRY FRONTIERS, 2018, 2 (05) :975-985
[44]   Incorporation of 2,6-Connected Azulene Units into the Backbone of Conjugated Polymers: Towards High-Performance Organic Optoelectronic Materials [J].
Xin, Hanshen ;
Ge, Congwu ;
Jiao, Xuechen ;
Yang, Xiaodi ;
Rundel, Kira ;
McNeill, Christopher R. ;
Gao, Xike .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) :1322-1326
[45]   Application of Azulene in Constructing Organic Optoelectronic Materials: New Tricks for an Old Dog [J].
Xin, Hanshen ;
Gao, Xike .
CHEMPLUSCHEM, 2017, 82 (07) :945-956
[46]   Biazulene diimides: a new building block for organic electronic materials [J].
Xin, Hanshen ;
Ge, Congwu ;
Yang, Xiaodi ;
Gao, Honglei ;
Yang, Xiaochun ;
Gao, Xike .
CHEMICAL SCIENCE, 2016, 7 (11) :6701-6705
[47]   Terazulene Isomers: Polarity Change of OFETs through Molecular Orbital Distribution Contrast [J].
Yamaguchi, Yuji ;
Takubo, Maki ;
Ogawa, Keisuke ;
Nakayama, Ken-ichi ;
Koganezawa, Tomoyuki ;
Katagiri, Hiroshi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (35) :11335-11343
[48]   Terazulene: A High-Performance n-Type Organic Field-Effect Transistor Based on Molecular Orbital Distribution Control [J].
Yamaguchi, Yuji ;
Ogawa, Keisuke ;
Nakayama, Ken-ichi ;
Ohba, Yoshihiro ;
Katagiri, Hiroshi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (51) :19095-19098
[49]   Synthesis, Properties, and OFET Characteristics of 5,5′-Di(2-azulenyl)-2,2′-bithiophene (DAzBT) and 2,5-Di(2-azulenyl)-thieno[3,2-b]thiophene (DAzTT) [J].
Yamaguchi, Yuji ;
Maruya, Yukihiro ;
Katagiri, Hiroshi ;
Nakayama, Ken-ichi ;
Ohba, Yoshihiro .
ORGANIC LETTERS, 2012, 14 (09) :2316-2319
[50]   Tuning the Semiconducting Behaviors of New Alternating Dithienyldiketopyrrolopyrrole-Azulene Conjugated Polymers by Varying the Linking Positions of Azulene [J].
Yao, Jingjing ;
Cai, Zhengxu ;
Liu, Zitong ;
Yu, Chenmin ;
Luo, Hewei ;
Yang, Yang ;
Yang, Sifen ;
Zhang, Guanxin ;
Zhang, Deqing .
MACROMOLECULES, 2015, 48 (07) :2039-2047
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