BIS(TETRATHIAFULVALENES) AND TRIS(TETRATHIAFULVALENES) (TTFS) DERIVED FROM REACTIONS OF THE TTF-THIOLATE ANION

被引:67
作者
BRYCE, MR
MARSHALLSAY, GJ
MOORE, AJ
机构
[1] Department of Chemistry, University of Durham
关键词
D O I
10.1021/jo00044a020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of new bis- and tris-TTF derivatives has been prepared using the TTF-thiolate anion 2 as a key intermediate. Thiolate anion 2 reacts with 2-bromoethanol to yield alcohol 3 from which the bis- and tris-TTF systems 4-7 have been obtained by reaction with the appropriate acid chloride. Subsequent reactions of the malonate anion of dimeric TTF 7 yield derivatives 8-10, which include the amphiphilic system 8. Thiolate anion 2 reacts with bis- and tris(bromomethyl)benzene to yield bis- and tris-TTF derivatives 11 and 12, respectively. Thioester 13, which serves as a shelf-stable precursor of thiolate anion 2, has been used in the synthesis of bis-TTF systems 17 and 18. The solution electrochemistry of the new multi-TTF derivatives has been studied by cyclic voltammetry, which reveals that the TTF moieties do not interact to any significant extent.
引用
收藏
页码:4859 / 4862
页数:4
相关论文
共 31 条
[1]   CONJUGATED TRIS-TETRATHIAFULVALENES [J].
ADAM, M ;
WOLF, P ;
RADER, HJ ;
MULLEN, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) :1624-1625
[2]   A FULLY CONJUGATED DIMERIC BEDT-TTF SYSTEM - SYNTHESIS, CRYSTAL-STRUCTURE, AND ELECTRICAL-PROPERTIES [J].
ADAM, M ;
BOHNEN, A ;
ENKELMANN, V ;
MULLEN, K .
ADVANCED MATERIALS, 1991, 3 (12) :600-602
[3]  
BECHGARD K, 1987, INTOR SYNTHETIC ELEC, P349
[4]   PREPARATION AND STRUCTURE OF A NOVEL ORGANOTELLURIUM DERIVATIVE - DI(TETRATHIAFULVALENE)TELLURIDE[(TTF)2TE] [J].
BECKER, JY ;
BERNSTEIN, J ;
BITTNER, S ;
SARMA, JARP ;
SHAHAL, L .
TETRAHEDRON LETTERS, 1988, 29 (47) :6177-6180
[5]   TETRATHIAFULVALENOPARACYCLOPHANES AND TETRATHIAFULVALENOPHANES [J].
BERTHOTHORAVAL, F ;
ROBERT, A ;
SOUIZI, A ;
BOUBEKEUR, K ;
BATAIL, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (13) :843-845
[6]   RECENT PROGRESS ON CONDUCTING ORGANIC CHARGE-TRANSFER SALTS [J].
BRYCE, MR .
CHEMICAL SOCIETY REVIEWS, 1991, 20 (03) :355-390
[7]   BIS(TETRATHIAFULVALENYL)SULPHIDE [(TTF)2S] - SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE [J].
BRYCE, MR ;
COOKE, G ;
DHINDSA, AS ;
ANDO, DJ ;
HURSTHOUSE, MB .
TETRAHEDRON LETTERS, 1992, 33 (13) :1783-1786
[8]  
BRYCE V, UNPUB VALUES E1 1 2
[9]   ELECTROACTIVE LANGMUIR-BLODGETT-FILMS OF O-HEXADECYLTHIOCARBOXYTETRATHIAFULVALENE (HDTTTF) [J].
DHINDSA, AS ;
BADYAL, JP ;
BRYCE, MR ;
PETTY, MC ;
MOORE, AJ ;
LVOV, YM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) :970-972
[10]  
FERRARO JR, 1987, INTOR SYNTHETIC ELEC