Alkynylated Phenazines: Synthesis, Characterization, and Metal-Binding Properties of Their Bis-Triazolyl Cycloadducts

被引：48

作者：

Bryant, Jonathan J. ^{[1
]}

Zhang, Yexiang ^{[2
,3
]}

Lindner, Benjamin D. ^{[1
]}

Davey, Evan A. ^{[2
]}

Appleton, Anthony Lucas ^{[2
]}

Qian, Xuhong ^{[3
]}

Bunz, U. H. F. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[3] E China Univ Sci & Technol, Sch Pharm, State Key Lab Bioreactor Engn, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 17期

基金：

美国国家科学基金会;

关键词：

CLICK-CHEMISTRY; 1.3-DIPOLARE CYCLOADDITIONEN; 1,3-DIPOLAR CYCLOADDITION; OPTICAL-PROPERTIES; ORGANISCHER AZIDE; BIOSYNTHESIS; CONSTRUCTION; LIGATION; SENSOR; BIS(BETA-CYCLODEXTRIN)S;

D O I：

10.1021/jo3012978

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have synthesized a series of ethynylated phenazines and their bis-triazolyl cycloadducts to serve as metal ion sensors. Binding of metal ions is achieved through coordination to the phenazine nitrogen atom and the triazole ring. To allow metal sensing in aqueous solution, the triazole units are substituted with water-soluble ethylene glycol chains. These phenazine cycloadducts exhibit a selective affinity for binding silver ions. Examination of the halogenated analogues reveals a lowering of the band gap and the corresponding bathochromic shifts in the absorption and emission spectra. The electron-withdrawing properties of these halogens also result in significantly decreased metal-binding activity of the phenazine cycloadducts.

引用

页码：7479 / 7486

页数：8

共 62 条

[31] Thiacalix[4]arene-cinnamaldehyde derivative: ICT-induced preferential nanomolar detection of Ag+ among different transition metal ions [J].

Kumar, Manoj ;

Kumar, Naresh ;

Bhalla, Vandana .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (09) :1769-1774

[32] Phenazine natural products: Biosynthesis, synthetic analogues, and biological activity [J].

Laursen, JB ;

Nielsen, J .

CHEMICAL REVIEWS, 2004, 104 (03) :1663-1685

[33] o-fluoranil chemistry:: Diels-Alder versus hetero-Diels-Alder cycloaddition [J].

Lemal, David A. ;

Ramanathan, Sudharsanam ;

Shellito, John .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3392-3396

[34] Synthesis and Optical Properties of Diaza- and Tetraazatetracenes [J].

Lindner, Benjamin D. ;

Engelhart, Jens U. ;

Maerken, Michaela ;

Tverskoy, Olena ;

Appleton, Anthony L. ;

Rominger, Frank ;

Hardcastle, Kenneth I. ;

Enders, Markus ;

Bunz, Uwe H. F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (15) :4627-4633

[35] Bridged bis(β-cyclodextrin)s possessing coordinated metal center(s) and their inclusion complexation behavior with model substrates:: Enhanced molecular binding ability by multiple recognition [J].

Liu, Y ;

Chen, Y ;

Li, L ;

Zhang, HY ;

Liu, SX ;

Guan, XD .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8518-8527

[36] Synthesis of bridged and metallobridged bis(β-cyclodextrin)s containing fluorescent oxamidobisbenzoyl linkers and their selective binding towards bile salts [J].

Liu, Yu ;

Yu, Hong-Mei ;

Chen, Yong ;

Zhao, Yan-Li .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (14) :3858-3868

[37] Orthogonal approaches to the simultaneous and cascade functionalization of macromolecules using click chemistry [J].

Malkoch, M ;

Thibault, RJ ;

Drockenmuller, E ;

Messerschmidt, M ;

Voit, B ;

Russell, TP ;

Hawker, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) :14942-14949

[38] Phenazine compounds in fluorescent Pseudomonas spp.: Biosynthesis and regulation [J].

Mavrodi, Dmitri V. ;

Blankenfeldt, Wulf ;

Thomashow, Linda S. .

ANNUAL REVIEW OF PHYTOPATHOLOGY, 2006, 44 :417-445

[39]

Medina B.M., 2007, J CHEM PHYS, V126, DOI DOI 10.1063/1.2713096

[40] Cu-catalyzed azide-alkyne cycloaddition [J].

Meldal, Morten ;

Tornoe, Christian Wenzel .

CHEMICAL REVIEWS, 2008, 108 (08) :2952-3015

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