四硫富瓦烯


























































































四硫富瓦烯



IUPAC名
2,2’-bis(1,3-dithiolylidene)
英文名
Tetrathiafulvalene
别名
 Δ2,2-bi-1,3-dithiole
识别

CAS号
31366-25-3  ✓

PubChem
99451

ChemSpider
89848

InChI


InChIKey
FHCPAXDKURNIOZ-UHFFFAOYAZ

ChEBI
52444
性质

化学式
C6H4S4

摩尔质量
 204.36 g·mol⁻¹
外观
 黄色固体

熔点
 116-119 °C

沸点
 分解

溶解性（其他）
 不溶于水，溶于有机溶剂
结构

偶极矩
 0 D
危险性

警示术语
 R：R43

安全术语
 S：S36/37
主要危害
 可燃
相关物质
相关化学品
TCNQ、噻吩
若非注明，所有数据均出自一般条件（25 ℃，100 kPa）下。

四硫富瓦烯（Tetrathiafulvalene，缩写：TTF），是富瓦烯的2,2'-位被硫原子替换后形成的有机硫化合物，化学分子式(H2C2S2C)2。它最早由Wudl在1970年合成，1972年发现其氯化物盐具高导电性，次年制得其TCNQ盐，并发现该盐的导电性在室温以下突然增加，在60K可达10^4 ohm^(-1) cm^(-1)，足以被称为“有机金属”。1979年又进一步发现以四硫富瓦烯为基础的Bechgaard盐[TMTSF]2X（X为PF6-,AsF6-）为首个制得的分子超导体，使得人们对这一领域产生极大兴趣。超过10,000个科学出版物讨论TTF及其衍生物。[1]


四硫富瓦烯虽然看上去是14π的平面系统，但缺乏环状共轭，所以不具芳香性。它可被氧化为自由基阳离子及双阳离子，均是热力学稳定和具芳香性的物种，氧化反应分步且可逆。四硫富瓦烯是强π电子供体，与受体如TCNQ形成的盐类是分子导体的典型代表，此类盐具高各向异性的导电性。



参看


  • Bechgaard盐


参考文献





  1. ^ Bendikov, M; Wudl, F; Perepichka, D. F. Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics. Chemical Reviews. 2004, 104 (11): 4891–4945. PMID 15535637. doi:10.1021/cr030666m. 









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