Dicyanovinyl Heterotetracenes: Synthesis, Solid-State Structures, and Photophysical Properties

被引:24
作者
Du, Chunyan [1 ,2 ]
Chen, Jianming [1 ,2 ]
Guo, Yunlong [1 ,2 ]
Lu, Kun [1 ,2 ]
Ye, Shanghui [1 ,2 ]
Zheng, Jian [1 ,2 ]
Liu, Yunqi [1 ]
Shuai, Zhigang [1 ]
Yu, Gui [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
THIN-FILM TRANSISTORS; FIELD-EFFECT TRANSISTORS; N-CHANNEL SEMICONDUCTORS; HIGH-MOBILITY; ORGANIC SEMICONDUCTOR; FUNCTIONALIZED ACENES; TRIETHYL PHOSPHITE; MOLECULAR PACKING; NITRO-COMPOUNDS; PERFORMANCE;
D O I
10.1021/jo901381f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two asymmetrically substituted dicyanovinyl heterotetracenes are synthesized and characterized. Single-crystal X-ray diffractions indicate both intermolecular hydrogen bonds and T-stacking existing in the solid-state structures. The solvatochromic behaviors of the two heterotetracenes were investigated in a variety of solvents. Both experimental and computational results suggest that the two heterotetracenes have low-lying lowest unoccupied molecular orbitals and thus may be potential n-type or bipolar organic semiconductors for organic electronics.
引用
收藏
页码:7322 / 7327
页数:6
相关论文
共 68 条
[1]   Studies of tetracene- and pentacene-based organic thin-film transistors fabricated by the neutral cluster beam deposition method [J].
Abthagir, PS ;
Ha, YG ;
You, EA ;
Jeong, SH ;
Seo, HS ;
Choi, JH .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (50) :23918-23924
[2]   V-Shaped 4,6-Bis(arylvinyl)pyrimidine Oligomers: Synthesis and Optical Properties [J].
Achelle, Sylvain ;
Nouira, Ines ;
Pfaffinger, Bernd ;
Ramondenc, Yvan ;
Ple, Nelly ;
Rodriguez-Lopez, Julian .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :3711-3717
[3]  
[Anonymous], ORGANOPHOSPHOROUS RE
[4]  
[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[5]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[6]   Thiazole and thiophene analogues of donor-acceptor stilbenes: Molecular hyperpolarizabilities and structure-property relationships [J].
Breitung, EM ;
Shu, CF ;
McMahon, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1154-1160
[7]   Hexathiapentacene: Structure, molecular packing, and thin-film transistors [J].
Briseno, Alejandro L. ;
Miao, Qian ;
Ling, Mang-Mang ;
Reese, Colin ;
Meng, Hong ;
Bao, Zhenan ;
Wudl, Fred .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15576-15577
[8]  
Cadogan J.I. G., 1969, SYNTHESIS, P11
[9]   REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .19. REDUCTION OF NITRO-COMPOUNDS BY TRIETHYL PHOSPHITE - A CONVENIENT NEW ROUTE TO CARBAZOLES INDOLES INDAZOLES TRIAZOLES AND RELATED COMPOUNDS [J].
CADOGAN, JIG ;
CAMERONW.M ;
MACKIE, RK ;
SEARLE, RJG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4831-&
[10]  
CADOGAN JIG, 1962, P CHEM SOC LONDON, P361