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Title: Fluoride Binding by a Neutral Organoantimony(V) Lewis Acid Embedded within a Dibenzodithiophene Chromophore
Organoantimony Lewis acids have been coveted for their ability to bind hard anions like fluoride in competing media. Herein, we describe the synthesis of a phenyl dithienostibole (1) in which the antimony(III) center is embedded within a planar dibenzodithiophene chromophore. Compound1reacts witho‐chloranil to form the corresponding catecholatostiborane (2); it also reacts withtert‐butyl peroxide in the presence of perfluoropinacol to form the corresponding pinacolatostiborane (3). Compound2was investigated as a platform for anion binding. UV–vis titrations in CH2Cl2afforded an association constant greater than 107 M−1pointing to the high fluoridophilicity of this new system. Density functional theory calculations highlight the role played by theσ*(Sb‐Cphenyl) orbital in imparting Lewis acidity to the antimony center of2.  more » « less
Award ID(s):
2108728
PAR ID:
10655515
Author(s) / Creator(s):
 ;  ;  ;  
Publisher / Repository:
Wiley-VCH GmbH, Weinheim
Date Published:
Journal Name:
Zeitschrift für anorganische und allgemeine Chemie
Volume:
651
Issue:
2
ISSN:
0044-2313
Page Range / eLocation ID:
e202400170
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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