ICCAS OpenIR
Synthesis, Crystal Structures, Optical Properties, and Photocurrent Response of Heteroacene Derivatives
Ren, Tiejun1; Xiao, Jinchong1; Wang, Wenying1; Xu, Wenya2; Wang, Sujuan1; Zhang, Xuemin1; Wang, Xuefei3; Chen, Hua1; Zhao, Jianwen2; Jiang, Li4
2014-07-01
Source PublicationCHEMISTRY-AN ASIAN JOURNAL
ISSN1861-4728
Volume9Issue:7Pages:1943-1949
AbstractSix 5,9,14,18-tetrathiaheptacene derivatives (1a-1f) were synthesized by using a simple ether-ether exchange reaction and fully characterized. In contrast to the planar conformation usually observed in thiophenefused benzene systems, single-crystal analysis indicates that 7,16-dipropyl-5,9,14,18-tetrathiaheptacene (1a), 7,16-diphenyl-5,9,14,18-tetrathiaheptacene (1b), and 7,16-di(4'-chlorophenyl)-5,9,14,18-tetrathiaheptacene (1c) adopt chair conformations. The as-formed dihedral angle between anthracene and the terminal benzene units are 137.258, 137.855, and 134.912 degrees for 1a, 1b, and 1c, respectively, which is close to the theoretical optimization results (1288 for 1b). Interestingly, the oxidized product of 7,16-di(trifluoromethylphenyl)-5,9,14,18-tetrathiaheptacene (1e) has a saddle shape, which results in the formation of column-shaped units in the single crystal. The substituents on the side phenyl group have less effect on their UV/Vis absorption spectra, but a distinct redshift that accounts for the intramolecular charge transfer can be observed in the emission spectra. The electrochemical measurements show that all compounds present two oxidation waves. The photoswitching behavior based on 1a-1f was further measured and the experimental results suggest that these heteroacene derivatives are promising semiconductor materials for organic electronics.
KeywordAcene Conformation Analysis Optical Properties Semiconductors X-ray Diffraction
DOI10.1002/asia.201402247
Indexed BySCI
Language英语
WOS IDWOS:000338017800027
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/50992
Collection中国科学院化学研究所
Corresponding AuthorXiao, Jinchong
Affiliation1.Hebei Univ, Key Lab Chem Biol Hebei Prov, Coll Chem & Environm Sci, Baoding 071002, Peoples R China
2.Chinese Acad Sci, Suzhou Inst Nanotech & Nanob, Printable Elect Res Ctr, Suzhou 215123, Peoples R China
3.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
4.Beijing Natl Lab Mol Sci, Lab Mol Nanostruct & Nanotechnol, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Ren, Tiejun,Xiao, Jinchong,Wang, Wenying,et al. Synthesis, Crystal Structures, Optical Properties, and Photocurrent Response of Heteroacene Derivatives[J]. CHEMISTRY-AN ASIAN JOURNAL,2014,9(7):1943-1949.
APA Ren, Tiejun.,Xiao, Jinchong.,Wang, Wenying.,Xu, Wenya.,Wang, Sujuan.,...&Jiang, Li.(2014).Synthesis, Crystal Structures, Optical Properties, and Photocurrent Response of Heteroacene Derivatives.CHEMISTRY-AN ASIAN JOURNAL,9(7),1943-1949.
MLA Ren, Tiejun,et al."Synthesis, Crystal Structures, Optical Properties, and Photocurrent Response of Heteroacene Derivatives".CHEMISTRY-AN ASIAN JOURNAL 9.7(2014):1943-1949.
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