"Janus" Calixarenes: Double-Sided Molecular Linkers for Facile, Multianchor Point, Multifunctional, Surface Modification

被引：19

作者：

Buttress, James P. ^{[1
]}

Day, David P. ^{[1
]}

Courtney, James M. ^{[1
]}

Lawrence, Elliot J. ^{[1
]}

Hughes, David L. ^{[1
]}

Blagg, Robin J. ^{[1
]}

Crossley, Alison ^{[2
]}

Matthews, Susan E. ^{[3
]}

Redshaw, Carl ^{[4
]}

Page, Philip C. Bulman ^{[1
]}

Wildgoose, Gregory G. ^{[1
]}

机构：

[1] Univ East Anglia, Sch Chem, Norwich Res Pk, Norwich NR4 7TJ, Norfolk, England

[2] Univ Oxford, Begbroke Sci Pk,Begbroke Hill, Oxford OX5 1PF, England

[3] Univ East Anglia, Sch Pharm, Norwich Res Pk, Norwich NR4 7TJ, Norfolk, England

[4] Univ Hull, Dept Chem, Cottingham Rd, Kingston Upon Hull HU6 7RX, N Humberside, England

来源：

LANGMUIR | 2016年 / 32卷 / 31期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

NANOTUBE-MODIFIED ELECTRODES; TRIAZOLE CLICK PRODUCTS; SOLID-PHASE SYNTHESIS; DIAZONIUM SALTS; GOLD SURFACES; COVALENT MODIFICATION; CARBON SURFACES; REDUCTION; ATTACHMENT; MONOLAYERS;

D O I：

10.1021/acs.langmuir.6b02222

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We herein report the synthesis of novel "Janus" calix[4]arenes bearing four "molecular tethering" functional groups on either the upper or lower rims of the calixarene. These enable facile multipoint covalent attachment to electrode surfaces with monolayer coverage. The other rim of the calixarenes bear either four azide or four ethynyl functional groups, which are easily modified by the copper(I)-catalyzed Oxidation azide-alkyne cycloaddition reaction (CuAAC), either pre- or postsurface modification, enabling these conical, nanocavity reactor sites to be decorated with a wide range of substrates to impart desired chemical properties. Redox active species decorating the peripheral rim are shown to be electrically connected by the calixarene to the electrode surface in either "up" or "down" orientations of the calixarene.

引用

页码：7806 / 7813

页数：8

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