Synthesis, characterization and optical properties of merocyanines derived from malononitrile dimer

被引:23
作者
Alias, Silvia
Andreu, Raquel
Angel Cerdan, Miguel
Franco, Santiago
Garin, Javier [1 ]
Orduna, Jesus
Romero, Pilar
Villacampa, Belen
机构
[1] Univ Zaragoza, CSIC, ICMA, Dept Quim Organ, E-50009 Zaragoza, Spain
[2] Univ Zaragoza, CSIC, ICMA, Dept Fis Mat Condensada, E-50009 Zaragoza, Spain
关键词
malononitrile dimer; merocyanines; proaromaticity; nonlinear optics;
D O I
10.1016/j.tetlet.2007.07.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between malononitrile dimer and 1,3-dithiole-derived polyenals affords push-pull systems with (Z)-geometry around the newly formed C=C bond. In one instance, an unexpected shortening of the merocyanine chain takes place. These push-pull derivatives have weakly alternated structures and moderate optical nonlinearities, which can be modified by functionalization of the amino group. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6539 / 6542
页数:4
相关论文
共 33 条
[1]  
Abd El Latif F M, 1999, J CHEM RES S, P696
[2]  
Akkurt M, 2000, CRYST RES TECHNOL, V35, P349, DOI 10.1002/1521-4079(200003)35:3<349::AID-CRAT349>3.0.CO
[3]  
2-Y
[4]  
AKKURT M, 1990, KRISTALLOGRAFIYA, V193, P315
[5]   Highly polarized dithiafulvenes:: synthesis and nonlinear optical properties [J].
Andreu, R ;
Aramburo, J ;
Cerdán, MA ;
Garín, J ;
Orduna, J ;
Villacampa, B .
TETRAHEDRON LETTERS, 2006, 47 (05) :661-664
[6]   Tuning first molecular hyperpolarizabilities through the use of proaromatic spacers [J].
Andreu, R ;
Blesa, MJ ;
Carrasquer, L ;
Garín, J ;
Orduna, J ;
Villacampa, B ;
Alcalá, R ;
Casado, J ;
Delgado, MCR ;
Navarrete, JTL ;
Allain, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8835-8845
[7]   Novel NLO-phores with proaromatic donor and acceptor groups [J].
Andreu, R ;
Garín, J ;
Orduna, J ;
Alcalá, R ;
Villacampa, B .
ORGANIC LETTERS, 2003, 5 (17) :3143-3146
[8]   Large quadratic hyperpolarizabilities with donor-acceptor polyenes exhibiting optimum bond length alternation: Correlation between structure and hyperpolarizability [J].
BlanchardDesce, M ;
Alain, V ;
Bedworth, PV ;
Marder, SR ;
Fort, A ;
Runser, C ;
Barzoukas, M ;
Lebus, S ;
Wortmann, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (07) :1091-1104
[9]  
Boila-Göckel A, 1999, J PRAK CHEM-CHEM ZTG, V341, P20, DOI 10.1002/(SICI)1521-3897(199901)341:1<20::AID-PRAC20>3.0.CO
[10]  
2-V