A facile organolithium route to ferrocene-based triarylmethyl dyes with substantial near IR and NLO properties

被引:21
作者
Arbez-Gindre, C
Steele, BR
Heropoulos, GA
Screttas, CG [1 ]
Communal, JE
Blau, WJ
Ledoux-Rak, I
机构
[1] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, Athens 11635, Greece
[2] Univ Dublin, Dept Phys, Dublin 2, Ireland
[3] Ecole Normale Super, Lab Photon Quant & Mol, F-94235 Cachan, France
关键词
near infrared; nonlinear optical materials; stilbene; carbenium ion; Halogen-metal exchange;
D O I
10.1016/j.jorganchem.2005.01.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of triarylmethanol derivatives containing combinations of phenyl, 1-naphthyl, 4-dimethylamino-4'-stilbenyl, ferrocenyl or 4-[2-ferrocenylethenyl]phenyl groups have been prepared by reaction of 4-[4-Me2NC6H4C=C]C6H4Li or 4-[FcC=C]C6H4Li (Fc = ferrocenyl) with ferrocenecarboxaldehyde, ferrocenyl phenyl ketone, methyl ferrocenecarboxylate, 1-naphthyl phenyl ketone, ethyl benzoate or diethyl carbonate. The carbinols readily form the corresponding intensely coloured carbenium ions in acid solution which have significant electronic absorption in the near infrared. Initial studies indicate that they also possess substantial first hyperpolarisabilities. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:1620 / 1626
页数:7
相关论文
共 23 条
[1]   The linear and non-linear optical properties of some conjugated ferrocene compounds with potent heterocyclic acceptors [J].
Alain, V ;
Fort, A ;
Barzoukas, M ;
Chen, CT ;
BlanchardDesce, M ;
Marder, SR ;
Perry, JW .
INORGANICA CHIMICA ACTA, 1996, 242 (1-2) :43-49
[2]   Organolithium reagents bearing nonlinear optical chromophores. Synthesis of triarylmethane dyes [J].
Arbez-Gindre, C ;
Screttas, CG ;
Fiorini, C ;
Schmidt, C ;
Nunzi, JM .
TETRAHEDRON LETTERS, 1999, 40 (41) :7413-7416
[3]   Studies of the electronic structure of metallocene-based second-order nonlinear optical dyes [J].
Barlow, S ;
Bunting, HE ;
Ringham, C ;
Green, JC ;
Bublitz, GU ;
Boxer, SG ;
Perry, JW ;
Marder, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3715-3723
[4]  
Cais M, 1966, ORGANOMET CHEM REV, V1, P435
[5]  
Daehne S., 1998, NEAR INFRARED DYES H
[6]   SYNTHESIS AND STRUCTURE OF (CIS)-[1-FERROCENYL-2-(4-NITROPHENYL)ETHYLENE], AN ORGANOTRANSITION METAL COMPOUND WITH A LARGE 2ND-ORDER OPTICAL NONLINEARITY [J].
GREEN, MLH ;
MARDER, SR ;
THOMPSON, ME ;
BANDY, JA ;
BLOOR, D ;
KOLINSKY, PV ;
JONES, RJ .
NATURE, 1987, 330 (6146) :360-362
[7]   Ferrocene in conjugation with a Fischer carbene: Synthesis, NLO, and electrochemical behavior of a novel organometallic push-pull system [J].
Jayaprakash, KN ;
Ray, PC ;
Matsuoka, I ;
Bhadbhade, MM ;
Puranik, VG ;
Das, PK ;
Nishihara, H ;
Sarkar, A .
ORGANOMETALLICS, 1999, 18 (19) :3851-3858
[8]   NEW ADVANCES IN MOLECULAR ENGINEERING FOR QUADRATIC NONLINEAR OPTICS [J].
LEDOUX, I .
SYNTHETIC METALS, 1993, 54 (1-3) :123-137
[9]   ORGANOMETALLIC COMPOUNDS FOR NONLINEAR OPTICS - THE SEARCH FOR EN-LIGHT-ENMENT [J].
LONG, NJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (01) :21-38
[10]   SPECTRAL BROADENING OF ELASTIC SECOND-HARMONIC LIGHT SCATTERING IN LIQUIDS [J].
MAKER, PD .
PHYSICAL REVIEW A-GENERAL PHYSICS, 1970, 1 (03) :923-+