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Dinaphthobenzo[1,2:4,5]dicyclobutadiene: Antiaromatic and Orthogonally Tunable Electronics and Packing

文献类型：期刊论文

作者Barker, Kayla P.2; Xia, Yan2; Jin, Zexin2; Yao, Ze-Fan1; Pei, Jian1
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2019-02-11
卷号58期号:7页码:2034-2039
关键词acenes annulations aromaticity polycycles semiconductors
ISSN号1433-7851
DOI10.1002/anie.201812581
通讯作者Pei, Jian(jianpei@pku.edu.cn) ; Xia, Yan(yanx@stanford.edu)
英文摘要Polycyclic conjugated hydrocarbons containing antiaromatic four-membered cyclobutadienoids (CDB) are of great fundamental and technical interest. However, their challenging synthesis has hampered the exploration and understanding of such systems. Reported herein is a modular and efficient synthesis of novel CBD-containing acene analogues, dinaphthobenzo[1,2:4,5]dicyclobutadiene (DNBDCs), with orthogonally tunable electronic properties and molecular packing. The design also features strong antiaromaticity of the CBD units, as revealed by nucleus-independent chemical shift and anisotropy of the induced current density calculations, as well as X-ray crystallography. Tuning the size of silyl substituents resulted in the most favorable brick-layer packing for triisobutylsilyl-DNBDC and a charge mobility of up to 0.52cm(2)V(-1)s(-1) in field-effect transistors.
WOS关键词PENTALENE DERIVATIVES ; PENTACENE ; SEMICONDUCTORS ; BIPHENYLENES ; CONSTRUCTION ; NANOGRAPHENE ; HETEROACENES ; AROMATICITY ; CYCLIZATION ; STRATEGY
资助项目Cottrell Scholar Award from Research Corporation for Science Advancement[24067] ; National Natural Science Foundation of China[21420102005] ; National Natural Science Foundation of China[21790360] ; National Natural Science Foundation of China[21722201] ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy[DE-AC02-05CH11231]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000458828000026
出版者WILEY-V C H VERLAG GMBH
资助机构Cottrell Scholar Award from Research Corporation for Science Advancement ; Cottrell Scholar Award from Research Corporation for Science Advancement ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Cottrell Scholar Award from Research Corporation for Science Advancement ; Cottrell Scholar Award from Research Corporation for Science Advancement ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Cottrell Scholar Award from Research Corporation for Science Advancement ; Cottrell Scholar Award from Research Corporation for Science Advancement ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Cottrell Scholar Award from Research Corporation for Science Advancement ; Cottrell Scholar Award from Research Corporation for Science Advancement ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy ; Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy
源URL[http://cas-ir.dicp.ac.cn/handle/321008/165968]  
专题大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者Xia, Yan; Pei, Jian
作者单位1.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem & Mol Engn, Beijing 100871, Peoples R China
2.Stanford Univ, Dept Chem, Stanford, CA 94305 USA
推荐引用方式
GB/T 7714		 Barker, Kayla P.,Xia, Yan,Jin, Zexin,et al. Dinaphthobenzo[1,2:4,5]dicyclobutadiene: Antiaromatic and Orthogonally Tunable Electronics and Packing[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(7):2034-2039.
APA Barker, Kayla P.,Xia, Yan,Jin, Zexin,Yao, Ze-Fan,&Pei, Jian.(2019).Dinaphthobenzo[1,2:4,5]dicyclobutadiene: Antiaromatic and Orthogonally Tunable Electronics and Packing.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(7),2034-2039.
MLA Barker, Kayla P.,et al."Dinaphthobenzo[1,2:4,5]dicyclobutadiene: Antiaromatic and Orthogonally Tunable Electronics and Packing".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.7(2019):2034-2039.

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来源：大连化学物理研究所

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