A Lewis Acidic, π-Conjugated Stibaindole with a Colorimetric Response to Anion Binding at Sb(III)

被引：41

作者：

Christianson, Anna M. ^{[1
]}

Gabbai, Francois P. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

ORGANOMETALLICS | 2017年 / 36卷 / 16期

基金：

美国国家科学基金会;

关键词：

OPTICAL-PROPERTIES; CRYSTAL-STRUCTURES; DRINKING-WATER; FLUORIDE; IONS;

D O I：

10.1021/acs.organomet.7b00419

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We describe 1-chloro-2,3-diphenylstibaindole (1-Cl), a Sb(III) heterocycle which exhibits visible-wavelength absorption due to conjugation of the sigma*(Sb-Cl) orbital with the pi* system of the conjugated backbone. Because the sigma*(Sb-Cl) orbital is accessible, stibaindole 1-Cl is a Lewis acid that readily binds halide anions at the site opposite the Sb-Cl bond. This binding induces a turn-off colorimetric response due to the suppression of the sigma*-pi* conjugation in the anion-bound form

引用

页码：3013 / 3015

页数：3

共 25 条

[1] From model compounds to extended π-conjugated systems:: Synthesis and properties of dithieno[3,2-b:2′,3′-d]phospholes [J].

Baumgartner, T ;

Bergmans, W ;

Kárpáti, T ;

Neumann, T ;

Nieger, M ;

Nyulászi, L .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) :4687-4699

[2] Organophosphorus π-conjugated materials [J].

Baumgartner, Thomas ;

Reau, Regis .

CHEMICAL REVIEWS, 2006, 106 (11) :4681-4727

[3] ZIRCONOCENE COMPLEXES OF UNSATURATED ORGANIC-MOLECULES - NEW VEHICLES FOR ORGANIC-SYNTHESIS [J].

BROENE, RD ;

BUCHWALD, SL .

SCIENCE, 1993, 261 (5129) :1696-1701

[4] A Mechanistic Study of Halogen Addition and Photoelimination from π-Conjugated Tellurophenes [J].

Carrera, Elisa I. ;

Lanterna, Anabel E. ;

Lough, Alan J. ;

Scaiano, Juan C. ;

Seferos, Dwight S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (08) :2678-2689

[5] Fluoride and cyanide anion sensing by an Sb(V)-substituted cyclometalated Ru polypyridyl complex [J].

Christianson, Anna M. ;

Gabbai, Francois P. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 847 :154-161

[6] 1λ5-Stibaindoles as Lewis Acidic, π-Conjugated, Fluoride Anion Responsive Platforms [J].

Christianson, Anna M. ;

Rivard, Eric ;

Gabbai, Francois P. .

ORGANOMETALLICS, 2017, 36 (14) :2670-2676

[7] Anion sensing with a Lewis acidic BODIPY-antimony(V) derivative [J].

Christianson, Anna M. ;

Gabbai, Francois P. .

CHEMICAL COMMUNICATIONS, 2017, 53 (16) :2471-2474

[8] SYNTHESIS OF MAIN GROUP HETEROCYCLES BY METALLACYCLE TRANSFER FROM ZIRCONIUM [J].

FAGAN, PJ ;

NUGENT, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2310-2312

[9] PHENYLCHLOROANTIMON(III)ATES - THEIR PREPARATIONS, AND THE CRYSTAL-STRUCTURES OF ME4N[PHSBCL3], [HPY]2[PHSBCL4], AND ME4N[PH2SBCL2] [J].

HALL, M ;

SOWERBY, DB .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 347 (1-2) :59-70

[10] Phosphorescence within benzotellurophenes and color tunable tellurophenes under ambient conditions [J].

He, Gang ;

Wiltshire, Benjamin D. ;

Choi, Paul ;

Savin, Aliaksandr ;

Sun, Shuai ;

Mohammadpour, Arash ;

Ferguson, Michael J. ;

McDonald, Robert ;

Farsinezhad, Samira ;

Brown, Alex ;

Shankar, Karthik ;

Rivard, Eric .

CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5444-5447

← 1 2 3 →