Heteroaromatic Cation-Based Chromophores: Synthesis and Nonlinear Optical Properties of Alkynylazinium Salts

被引:9
作者
Caneque, Tatiana [1 ]
Cuadro, Ana M. [1 ]
Alvarez-Builla, Julio [1 ]
Perez-Moreno, Javier [2 ]
Clays, Koen [2 ]
Marcelo, Gema [3 ]
Mendicuti, Francisco [3 ]
Castano, Obis [3 ]
Andres, Jose L. [3 ]
Vaquero, Juan J. [1 ]
机构
[1] Univ Alcala, Dept Quim Organ, Madrid 28871, Spain
[2] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium
[3] Univ Alcala, Dept Quim Fis, Madrid 28871, Spain
关键词
Heterocycles; Cations; Chromophores; Synthesis; Nonlinear optics; FREQUENCY-DEPENDENT HYPERPOLARIZABILITIES; HYPER-RAYLEIGH SCATTERING; ELECTRON-ACCEPTOR; 2ND-ORDER NONLINEARITIES; 2ND-HARMONIC GENERATION; SONOGASHIRA REACTION; NLO PROPERTIES; ORGANIC SALTS; DESIGN; DERIVATIVES;
D O I
10.1002/ejoc.201000816
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of alkynylazinium cationic (D-pi-A(+)) chromophores were prepared in good yields by the reaction of bromoazinium (pyridinium, quinolinium, and isoquinolinium iodides) with alkynes under Sonogashira conditions. The analysis of the experimentally recorded spectra is supported by quantum chemical calculations using restricted configuration interaction and density functional methods. First-order hyper-polarizabilities of (D-pi-A(+)) azinium-based cations as a new class of second-order nonlinear optical (NLO) chromophores were also studied by hyper-Rayleigh scattering experiments and computational procedures.
引用
收藏
页码:6323 / 6330
页数:8
相关论文
共 54 条
[1]  
[Anonymous], 2006, Non-linear optical properties of matter
[2]  
Barlow S., 2007, FUNCTIONAL ORGANIC M, P393
[3]   New NLO stilbene derivatives bearing phosphonate ester electron-withdrawing groups [J].
Belfield, KD ;
Chinna, C ;
Schafer, KJ .
TETRAHEDRON LETTERS, 1997, 38 (35) :6131-6134
[4]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[5]   Second-order nonlinearities and crystal structures of methylsulfonyl- and phenylsulfonyl-substituted thiophene imino dyes [J].
Chou, SSP ;
Sun, DJ ;
Lin, HC ;
Yang, PK .
CHEMICAL COMMUNICATIONS, 1996, (09) :1045-1046
[6]   Synthesis and second-order nonlinearities of sulfonyl-substituted pyrrole imino dyes [J].
Chou, SSP ;
Hsu, GT ;
Lin, HC .
TETRAHEDRON LETTERS, 1999, 40 (11) :2157-2160
[7]   HYPER-RAYLEIGH SCATTERING IN SOLUTION [J].
CLAYS, K ;
PERSOONS, A .
PHYSICAL REVIEW LETTERS, 1991, 66 (23) :2980-2983
[8]   Design strategies versus limiting theory for engineering large second-order nonlinear optical polarizabilities in charged organic molecules [J].
Clays, K ;
Coe, BJ .
CHEMISTRY OF MATERIALS, 2003, 15 (03) :642-648
[9]   HYPER-RAYLEIGH SCATTERING IN SOLUTION [J].
CLAYS, K ;
PERSOONS, A .
REVIEW OF SCIENTIFIC INSTRUMENTS, 1992, 63 (06) :3285-3289
[10]   Switchable nonlinear optical metallochromophores with pyridinium electron acceptor groups [J].
Coe, Benjamin J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (06) :383-393