Decorating Tetrathiafulvalene (TTF) with Fluorinated Phenyls through Sulfur Bridges: Facile Synthesis, Properties, and Aggregation through Fluorine Interactions

doi:10.1002/chem.201402327

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	Decorating Tetrathiafulvalene (TTF) with Fluorinated Phenyls through Sulfur Bridges: Facile Synthesis, Properties, and Aggregation through Fluorine Interactions
	Lu, Xiaofeng 1,2; Sun, Jibin 1,2; Liu, Yu 1,2; Shao, Jiafeng 3; Ma, Longfei 1,2; Zhang, Shangxi 1,2; Zhao, Jinlian 1,2; Shao, Yongliang 1,2; Zhang, Hao-Li 1,2; Wang, Zhaohui 4
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2014-07-28
卷号	20 期号:31 页码:9650-9656
关键词	C-s Coupling Electrochemistry Fluorine Interactions Photochemistry Ttf Derivatives
ISSN号	0947-6539
DOI	10.1002/chem.201402327
英文摘要	Tetrathiafulvalene derivatives (TTF1-TTF9) bearing fluorinated phenyl groups attached through the sulfur bridges have been synthesized by employing a copper-mediated C-S coupling reaction of C6H5-xFxI (x=1, 2, 5) and a zinc-thiolate complex, (TBA)(2)[Zn(DMIT)(2)] (TBA=tetrabutyl ammonium, DMIT=1,3-dithiole-2-thione-4,5-dithiolate), as the key step. Particularly, the selective synthesis of C6F5-substituted (TTF8) and C6F4-fused (TTF9) TTFs from C6F5I is disclosed. The physicochemical properties and crystal structures of these TTFs are fully investigated by UV/Vis absorption spectra, cyclic voltammetry, molecular orbital calculation, and single-crystal X-ray diffraction. The exchange of hydrogen versus fluorine on the peripheral phenyl groups show a notable influence on both the electronic and crystallographic natures of the resulting TTFs: 1) lowering both the HOMO and the LUMO energy levels, 2) modulating the electrochemical properties by regioselective and/or the degree of fluorination, 3) enhancing the driving forces of stacking by multiple fluorine interactions (F...S, C-F...pi/pi(F), C-F...F-C, and C-F...H). This work indicates that the decoration with fluorinated phenyls holds promise to produce functional TTFs with novel electronic and aggregation features.
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000340176600026
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/52503]
专题	中国科学院化学研究所
通讯作者	Shao, Xiangfeng
作者单位	1.Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China 2.Lanzhou Univ, Sch Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China 3.Lanzhou Univ, Sch Phys Sci & Technol, Lanzhou 730000, Gansu, Peoples R China 4.Chinese Acad Sci, Inst Chem, Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Lu, Xiaofeng,Sun, Jibin,Liu, Yu,et al. Decorating Tetrathiafulvalene (TTF) with Fluorinated Phenyls through Sulfur Bridges: Facile Synthesis, Properties, and Aggregation through Fluorine Interactions[J]. CHEMISTRY-A EUROPEAN JOURNAL,2014,20(31):9650-9656.
APA	Lu, Xiaofeng.,Sun, Jibin.,Liu, Yu.,Shao, Jiafeng.,Ma, Longfei.,...&Shao, Xiangfeng.(2014).Decorating Tetrathiafulvalene (TTF) with Fluorinated Phenyls through Sulfur Bridges: Facile Synthesis, Properties, and Aggregation through Fluorine Interactions.CHEMISTRY-A EUROPEAN JOURNAL,20(31),9650-9656.
MLA	Lu, Xiaofeng,et al."Decorating Tetrathiafulvalene (TTF) with Fluorinated Phenyls through Sulfur Bridges: Facile Synthesis, Properties, and Aggregation through Fluorine Interactions".CHEMISTRY-A EUROPEAN JOURNAL 20.31(2014):9650-9656.