SYNTHESIS AND CHARACTERIZATION OF SOME 1,4,8,11,15,18,22,25-OCTA-ALKYL-22,25-BIS(CARBOXYPROPYL)PHTHALOCYANINES AND 1,4,8,11,15,18-HEXA-ALKYL-22,25-BIS(CARBOXYPROPYL)PHTHALOCYANINES

被引:149
作者
MCKEOWN, NB [1 ]
CHAMBRIER, I [1 ]
COOK, MJ [1 ]
机构
[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 04期
关键词
D O I
10.1039/p19900001169
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 3,6-dialkylphthalonitriles and 3,6-bis(4,4,4-trimethoxybutyl) phthalonitrite have been prepared via Diels-Alder reactions of 2,5-disubstituted furans or thiophene 1,1-dioxides with fumaro-nitrile. The phthalonitriles were converted into the title phthalocyanines as metal-free and copper(II) derivatives. The macrocycles were characterised using 1H NMR and optical spectroscopy, and fast-atom bombardment mass spectrometry. Certain examples exhibit discotic liquid crystal behaviour.
引用
收藏
页码:1169 / 1177
页数:9
相关论文
共 44 条
[1]   ESR AND ELECTRONIC SPECTRAL INVESTIGATION OF SELF-ASSOCIATION OF PHTHALOCYANINE DYES IN SOLUTION [J].
ABKOWITZ, M ;
MONAHAN, AR .
JOURNAL OF CHEMICAL PHYSICS, 1973, 58 (06) :2281-2287
[2]   PHTHALOCYANINE LANGMUIR BLODGETT-FILM GAS DETECTOR [J].
BAKER, S ;
ROBERTS, GG ;
PETTY, MC .
IEE PROCEEDINGS-I COMMUNICATIONS SPEECH AND VISION, 1983, 130 (05) :260-263
[3]   THE PREPARATION AND PROPERTIES OF STABLE METAL-FREE PHTHALOCYANINE LANGMUIR-BLODGETT FILMS [J].
BAKER, S ;
PETTY, MC ;
ROBERTS, GG ;
TWIGG, MV .
THIN SOLID FILMS, 1983, 99 (1-3) :53-59
[4]   GAP PHTHALOCYANINE LANGMUIR-BLODGETT FILM ELECTROLUMINESCENT DIODE [J].
BATEY, J ;
PETTY, MC ;
ROBERTS, GG ;
WIGHT, DR .
ELECTRONICS LETTERS, 1984, 20 (12) :489-491
[6]  
BUCHTA E, 1965, LIEBIGS ANN CHEM, V686, P77
[7]   ALKYLATION REACTIONS OF PROPARGYL ALCOHOL - IMPROVED ROUTES TO PROSTAGLANDIN ALPHA-SIDE CHAIN PRECURSORS [J].
CASY, G ;
FURBER, M ;
RICHARDSON, KA ;
STEPHENSON, GR ;
TAYLOR, RJK .
TETRAHEDRON, 1986, 42 (21) :5849-5856
[8]   HIGH-YIELD SYNTHESES OF DILITHIO-DERIVATIVES OF FURAN, THIOPHENE, N-METHYLPYRROLE, 3-METHYLFURAN, AND 3-METHYLTHIOPHEN - APPLICATION OF METHOD TO 2-METHYLFURAN, 2-METHYLTHIOPHEN, 2,5-DIMETHYLFURAN, 2,5-DIMETHYLTHIOPHEN, BENZO[B]FURAN, BENZO[B]THIOPHEN, PYRROLE, AND INDOLE [J].
CHADWICK, DJ ;
WILLBE, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :887-893
[9]   SYNTHESIS AND MORPHOLOGY OF NEW DISCOGENIC PHTHALOCYANINE DERIVATIVES [J].
CHO, IH ;
LIM, YS .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1988, 154 :9-26
[10]   1,4,8,11,15,18-HEXA-ALKYL-22,25-BIS(CARBOXYPROPYL)PHTHALOCYANINES - MATERIALS DESIGNED FOR DEPOSITION AS LANGMUIR-BLODGETT-FILMS [J].
COOK, MJ ;
DANIEL, MF ;
HARRISON, KJ ;
MCKEOWN, NB ;
THOMSON, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) :1148-1150