Synthesis of electroactive hydrazones derived from 3-(10-alkyl-10H-phenothiazin-3-yl)-2-propenals and their corresponding 3,3′-bispropenals

被引：19

作者：

Bieliauskas, Aurimas ^{[1
]}

Martynaitis, Vytas ^{[2
]}

Getautis, Vytautas ^{[2
]}

Malinauskas, Tadas ^{[2
]}

Jankauskas, Vygintas ^{[3
]}

Kamarauskas, Egidijus ^{[3
]}

Holzer, Wolfgang ^{[4
]}

Sackus, Algirdas ^{[1
,2
]}

机构：

[1] Kaunas Univ Technol, Inst Synthet Chem, LT-50254 Kaunas, Lithuania

[2] Kaunas Univ Technol, Dept Organ Chem, Fac Chem Technol, LT-50254 Kaunas, Lithuania

[3] Vilnius Univ, Dept Solid State Elect, LT-10222 Vilnius, Lithuania

[4] Univ Vienna, Dept Drug & Nat Prod Synth, Fac Life Sci, A-1090 Vienna, Austria

来源：

TETRAHEDRON | 2012年 / 68卷 / 18期

关键词：

Phenothiazine; Acrylaldehydes; Hydrazones; Ionisation potentials; Charge transport; ACROLEIN-DIETHYL-ACETAL; 3-COMPONENT DOMINO SYNTHESIS; CATALYZED HECK ARYLATION; LIGHT-EMITTING-DIODES; 3-ARYLPROPIONIC ACIDS; CONJUGATED POLYMERS; BUTADIENYL DYES; PHENOTHIAZINE; CINNAMALDEHYDES; DERIVATIVES;

D O I：

10.1016/j.tet.2012.03.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-(10-Alkyl-10H-phenothiazin-3-yl)-2-propenals and their corresponding 3,3'-bispropenals that represent a previously unexplored class of functionalised phenothiazine derivatives were prepared upon reacting N-alkylated 3-bromo- and 3,7-dibromo-10H-phenothiazines with acrolein diethyl acetal under Pd catalysis. The obtained heterocyclic 2,3-unsaturated aldehydes were condensed with N-methyl-N-phenylhydrazine and N,N-diphenylhydrazine resulting in mono- and dihydrazones that act as effective hole transporting materials. Thermal, optical, electrochemical and photophysical properties of the synthesised new organic electroactive derivatives have been investigated. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3552 / 3559

页数：8

共 66 条

[1] Acrolein diethyl acetal:: A three-carbon homologating reagent for the synthesis of β-arylpropanoates and cinnamaldehydes by Heck reaction catalyzed by a Kaiser oxime resin derived palladacycle [J].