Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection

被引：21

作者：

Granzhan, Anton ^{[1
]}

Teulade-Fichou, Marie-Paule ^{[1
]}

机构：

[1] CNRS, Inst Curie, Ctr Rech, UMR176, F-91405 Orsay, France

来源：

TETRAHEDRON | 2009年 / 65卷 / 07期

关键词：

MOLECULAR RECOGNITION; ACETALIZATION;

D O I：

10.1016/j.tet.2008.12.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Three bibrachial cyclobisintercaland-type macrocycles with a 2,6-naphthylene scaffold and pyrene. ferrocene, or primary amino groups in side chains were synthesized by a [2 + 2]cyclocondensation of functionalized diethylenetriamine derivatives with naphthalene-2,6-dialdehyde, whereas their monobrachial counterparts were prepared by a [1+1]-cyclocondensation of polyamines with a corresponding dialdehyde building block. The pyrene-functionalized macrocycles are able to bind orthophthalate and terephthalate anions in aqueous medium, as monitored by the changes in their fluorescence (excimer or monomer) properties. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1349 / 1360

页数：12

共 33 条

[1]

A NOVEL-APPROACH TO DUAL-ACTING THROMBOXANE RECEPTOR ANTAGONIST AND SYNTHASE INHIBITORS BASED ON THE LINK OF 1,3-DIOXANE-THROMBOXANE RECEPTOR ANTAGONISTS AND 1,3-DIOXANE-THROMBOXANE SYNTHASE INHIBITORS [J].

ACKERLEY, N ;

BREWSTER, AG ;

BROWN, GR ;

CLARKE, DS ;

FOUBISTER, AJ ;

GRIFFIN, SJ ;

HUDSON, JA ;

SMITHERS, MJ ;

WHITTAMORE, PRO .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (10) :1608-1628

[2]

Synthesis and coordination properties of an azamacrocyclic Zn(II) chemosensor containing pendent methylnaphthyl groups [J].

Alarcon, Javier ;

Albelda, M. Teresa ;

Belda, Raquel ;

Clares, M. Paz ;

Delgado-Pinar, Estefania ;

Frias, Juan C. ;

Garcia-Espana, Enrique ;

Gonzalez, Jorge ;

Soriano, Conxa .

DALTON TRANSACTIONS, 2008, (46) :6530-6538

[3]

Selective recognition of pyrimidine-pyrimidine DNA mismatches by distance-constrained macrocyclic bis-intercalators [J].

Bahr, Matthias ;

Gabelica, Valerie ;

Granzhan, Anton ;

Teulade-Fichou, Marie-Paule ;

Weinhold, Elmar .

NUCLEIC ACIDS RESEARCH, 2008, 36 (15) :5000-5012

[4]

Synthesis and assembly of monofunctionalized pyrogallolarene capsules monitored by fluorescence resonance energy transfer [J].

Barrett, Elizabeth S. ;

Dale, Trevor J. ;

Rebek, Julius, Jr. .

CHEMICAL COMMUNICATIONS, 2007, (41) :4224-4226

[5]

Optimizing saccharide-directed molecular delivery to biological receptors:: Design, synthesis, and biological evaluation of glycodendrimer -: Cyclodextrin conjugates [J].

Benito, JM ;

Gömez-García, M ;

Mellet, CO ;

Baussanne, I ;

Defaye, J ;

Fernández, JMG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10355-10363

[6]

BOEV VI, 1992, ZH OBSHCH KHIM+, V62, P1330

[7]

Structure/activity study of tris(2-aminoethyl)amine-derived translocases for phosphatidylcholine [J].

Boon, JM ;

Lambert, TN ;

Smith, BD ;

Beatty, AM ;

Ugrinova, V ;

Brown, SN .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2168-2174

[8]

Metal-free methods in the synthesis of macrocyclic Schiff bases [J].

Borisova, Nataliya E. ;

Reshetova, Marina D. ;

Ustynyuk, Yuri A. .

CHEMICAL REVIEWS, 2007, 107 (01) :46-79

[9]

Cesario M, 1998, MOLECULAR RECOGNITION AND INCLUSION, P279

[10]

Specific interaction of citrate with bis(fluorophoric) bibrachial lariat aza-crown in comparison with the other components of the Krebs cycle [J].

Clares, M. Paz ;

Lodeiro, Carlos ;

Fernandez, Damian ;

Parola, A. Jorge ;

Pina, Fernando ;

Garcia-Espana, Enrique ;

Soriano, Conxa ;

Tejero, Roberto .

CHEMICAL COMMUNICATIONS, 2006, (36) :3824-3826

← 1 2 3 4 →