Oligo(furan-2,5-diylvinylene)s as pi-conjugating spacers in linearly extended hybrid tetrathiafulvalene analogues

被引:20
作者
Elandaloussi, EH
Frere, P
BenahmedGasmi, A
Riou, A
Gorgues, A
Roncali, J
机构
[1] UNIV ANGERS,CNRS,EP 66,F-49045 ANGERS,FRANCE
[2] UNIV ORAN,CHIM ORGAN LAB,ES SENIA 31000,ALGERIA
关键词
D O I
10.1039/jm9960601859
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis of a new series of push-push systems based on furan-2,5-diylvinylene oligomers end-capped with 1,3-dithiol-2-ylidene electron-releasing groups is described. H-1 NMR spectroscopy and X-ray diffraction reveal that the molecules adopt a planar conformation stabilized by strong intramolecular interactions. Electronic absorption spectroscopy indicates that the effective conjugation length increases steadily with the length of the pi-conjugated system without any evidence of saturation. Analysis of electrochemical behaviour by cyclic voltammetry shows that, whereas all compounds are easily oxidized into stable dications, with extension of the conjugation length the oxidation process progressively evolves from two successive one-electron steps to a single step two-electron transfer.
引用
收藏
页码:1859 / 1863
页数:5
相关论文
共 33 条
[21]  
Nguyen TT, 1996, B SOC CHIM FR, V133, P301
[22]  
NGUYEN TT, 1995, J MOD OPTIC, V42, P2095
[23]   KETENE DITHIOACETAL AS A PI-ELECTRON DONOR IN 2ND-ORDER NONLINEAR-OPTICAL CHROMOPHORES [J].
RAO, VP ;
CAI, YM ;
JEN, AKY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (14) :1689-1690
[24]   DRAMATICALLY ENHANCED 2ND-ORDER NONLINEAR-OPTICAL SUSCEPTIBILITIES IN TRICYANOVINYLTHIOPHENE DERIVATIVES [J].
RAO, VP ;
JEN, AKY ;
WONG, KY ;
DROST, KJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) :1118-1120
[25]   NOVEL PUSH-PULL THIOPHENES FOR 2ND-ORDER NONLINEAR OPTICAL APPLICATIONS [J].
RAO, VP ;
JEN, AKY ;
WONG, KY ;
DROST, KJ .
TETRAHEDRON LETTERS, 1993, 34 (11) :1747-1750
[26]   EFFECTS OF STRUCTURE ON THE OPTICAL AND REDOX PROPERTIES OF THE OLIGOTHIOPHENE - TETRATHIAFULVALENE HYBRID SYSTEM [J].
RONCALI, J ;
RASMUSSEN, L ;
THOBIEGAUTIER, C ;
FRERE, P ;
BRISSET, H ;
SALLE, M ;
BECHER, J ;
SIMONSEN, O ;
HANSEN, TK ;
BENAHMEDGASMI, A ;
ORDUNA, J ;
GARIN, J ;
JUBAULT, M ;
GORGUES, A .
ADVANCED MATERIALS, 1994, 6 (11) :841-845
[27]   EXTENSIVELY CONJUGATED TETRATHIAFULVALENE (TTF) PI-ELECTRON DONORS WITH OLIGOTHIOPHENES SPACER GROUPS [J].
RONCALI, J ;
GIFFARD, M ;
FRERE, P ;
JUBAULT, M ;
GORGUES, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (08) :689-691
[28]   PRECURSOR COMPOUNDS FOR ORGANIC METALS AND NONLINEAR OPTICAL-DEVICES FROM CARBOHYDRATE-DERIVED HYDROXYMETHYLFURFURALDEHYDE - FURANOID ELECTRON-DONORS AND PUSH-PULL SUBSTITUTED COMPOUNDS [J].
SCHOBERL, U ;
SALBECK, J ;
DAUB, J .
ADVANCED MATERIALS, 1992, 4 (01) :41-44
[29]  
Schukat G., 1987, SULFUR REPORTS, V7, P155, DOI DOI 10.1080/01961778708082503
[30]  
SEEBOTH H, 1977, Z CHEM, V16, P399