The six-membered-ring azomethine N-((E)-{5-[(E)-(pyridin-3-ylimino)methyl]thiophen-2-yl}methylidene)pyridin-3-amine

被引：4

作者：

Bolduc, Andreanne ^{[1
]}

Dufresne, Stephane ^{[1
]}

Skene, W. G. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2013年 / 69卷

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

crystal structure; hydrogen bonding; pi-stacking interactions; azomethines; optical properties; electrochemical properties; ELECTROCHEMICAL CHARACTERIZATION; MOLECULAR-STRUCTURE; CRYSTAL;

D O I：

10.1107/S0108270113024566

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The title compound, C16H12N4S, forms a three-dimensional layered network structure via intermolecular hydrogen bonding and pi-stacking. The azomethine molecule adopts the thermodynamically stable E regioisomer and the pyridine substituents are antiperiplanar. The mean planes of the pyridine rings and the azomethine group to which they are connected are twisted by 27.27 (5) and 33.60 (5)degrees. The electrochemical energy gap of 2.3 eV based on the HOMO-LUMO energy difference is in agreement with the spectroscopically derived value.

引用

页码：1196 / +

页数：9

共 24 条

[1]

[Anonymous], 2007, APEX2

[2]

[Anonymous], 2001, SHELXTL

[3]

[Anonymous], 2004, SAINT

[4] Survey of recent advances of in the field of π-conjugated heterocyclic azomethines as materials with tuneable properties [J].

Bolduc, Andreanne ;

Mallet, Charlotte ;

Skene, W. G. .

SCIENCE CHINA-CHEMISTRY, 2013, 56 (01) :3-23

[5] Chemical doping of EDOT azomethine derivatives: insight into the oxidative and hydrolytic stability [J].

Bolduc, Andreanne ;

Dufresne, Stephane ;

Skene, W. G. .

JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (11) :5053-5064

[6] EDOT-containing azomethine: an easily prepared electrochromically active material with tuneable colours [J].

Bolduc, Andreanne ;

Dufresne, Stephane ;

Skene, W. G. .

JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (23) :4820-4826

[7] Photophysical, crystallographic, and electrochemical characterization of novel conjugated thiopheno azomethines [J].

Bourgeaux, Marie ;

Perez Guarin, Sergio Andres ;

Skene, W. G. .

JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (10) :972-979

[8] CRYSTAL AND MOLECULAR STRUCTURES OF BENZYLIDENEANILINE, BENZYLIDENEANILINE PARA CARBOXYLIC ACID AND PARA METHYLBENZYLIDENE PARA NITROANILINE [J].

BURGI, HB ;

DUNITZ, JD .

HELVETICA CHIMICA ACTA, 1970, 53 (07) :1747-&

[9] Unsymmetric pyrrole, thiophene, and furan-conjugated comonomers prepared using azomethine connections: Potential new monomers for alternating homocoupled products [J].

Dufresne, Stephane ;

Skene, W. G. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10) :3859-3866

[10] (E)-5-(2-Thienylmethyleneamino)-quinolin-8-ol [J].

Dufresne, Stephane ;

Bourque, Alex N. ;

Skene, W. G. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 :O316-U5448

← 1 2 3 →