Acyclic indole and carbazole-based sulfate receptors

被引：120

作者：

Gale, Philip A. ^{[1
]}

Hiscock, Jennifer R. ^{[1
]}

Jie, Chen Zhu ^{[1
,2
]}

Hursthouse, Michael B. ^{[1
]}

Light, Mark E. ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

[2] Raffles Inst, Jr Coll, Singapore 575954, Singapore

来源：

CHEMICAL SCIENCE | 2010年 / 1卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

BINDING PROTEIN; SALMONELLA-TYPHIMURIUM; ANION COMPLEXATION; AQUEOUS-SOLUTION; MACROCYCLES; RECOGNITION; TRANSPORT; 1,3-DIINDOLYLUREAS; EXTRACTANTS; TEMPLATION;

D O I：

10.1039/c0sc00202j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The anion complexation properties of a series of acyclic receptors consisting of diindolylurea groups appended with amide, amidoindole or amidocarbazole groups have been studied. The receptors selectively bind and encapsulate sulfate via either six or eight hydrogen bonds. Receptors containing eight hydrogen bond donors perturb the pK(a) of bound dihydrogen phosphate and bicarbonate to the extent that they are deprotonated by free anion in solution.

引用

页码：215 / 220

页数：6

共 43 条

[1] 2,7-functionalized indoles as receptors for anions [J].

Bates, Gareth W. ;

Triyanti ;

Light, Mark E. ;

Albrecht, Markus ;

Gale, Philip A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) :8921-8927

[2] Isophthalamides and 2,6-dicarboxamidopyridines with pendant indole groups: a 'twisted' binding mode for selective fluoride recognition [J].

Bates, Gareth W. ;

Gale, Philip A. ;

Light, Mark E. .

CHEMICAL COMMUNICATIONS, 2007, (21) :2121-2123

[3] Anion receptor chemistry: highlights from 2007 [J].

Caltagirone, Claudia ;

Gale, Philip A. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) :520-563

[4] 1,3-Diindolylureas: high affinity dihydrogen phosphate receptors [J].

Caltagirone, Claudia ;

Gale, Philip A. ;

Hiscock, Jennifer R. ;

Brooks, Simon J. ;

Hursthouse, Michael B. ;

Light, Mark E. .

CHEMICAL COMMUNICATIONS, 2008, (26) :3007-3009

[5] Metal-induced pre-organisation for anion recognition in a neutral platinum-containing receptor [J].

Caltagirone, Claudia ;

Mulas, Andrea ;

Isaia, Francesco ;

Lippolis, Vito ;

Gale, Philip A. ;

Light, Mark E. .

CHEMICAL COMMUNICATIONS, 2009, (41) :6279-6281

[6] 1,3-Diindolylureas and 1,3-Diindolythioureas: Anion Complexation studies in Solution and the Solid State [J].

Caltagirone, Claudia ;

Hiscock, Jennifer R. ;

Hursthouse, Michael B. ;

Light, Mark E. ;

Gale, Philip A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (33) :10236-10243

[7] Indole-based macrocycles as a class of receptors for anions [J].

Chang, KJ ;

Moon, D ;

Lah, MS ;

Jeong, KS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7926-7929

[8] Oligoindole-based foldamers with a helical conformation induced by chloride [J].

Chang, KJ ;

Kang, BN ;

Lee, MH ;

Jeong, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12214-12215

[9] Sulfate anion templation of a neutral pseudorotaxane assembly using an indolocarbazole threading component [J].

Chmielewski, Michal J. ;

Zhao, Liyun ;

Brown, Asha ;

Curiel, David ;

Sambrook, Mark R. ;

Thompson, Amber L. ;

Santos, Sergio M. ;

Felix, Vitor ;

Davis, Jason J. ;

Beer, Paul D. .

CHEMICAL COMMUNICATIONS, 2008, (27) :3154-3156

[10] 1,8-diamino-3,6-dichlorocarbazole: A promising building block for anion receptors [J].

Chmielewski, MJ ;

Charon, M ;

Jurczak, J .

ORGANIC LETTERS, 2004, 6 (20) :3501-3504

← 1 2 3 4 5 →