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Crown-annelated 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives as cation sensors: Synthesis, X-ray crystal structures, voltammetric and spectroscopic monitoring of metal complexation

Bryce, MR and Batsanov, AS and Finn, T and Hansen, TK and Moore, AJ and Howard, JAK and Kamenjicki, M and Lednev, IK and Asher, SA (2001) Crown-annelated 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives as cation sensors: Synthesis, X-ray crystal structures, voltammetric and spectroscopic monitoring of metal complexation. European Journal of Organic Chemistry (5). 933 - 940. ISSN 1434-193X

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Abstract

The synthesis of O4S2-crown annelated derivatives of 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene using the novel Horner-Wadsworth-Emmons reagent 7 is reported. The bis- and mono-crown systems 9 and 12 function as efficient ligands in the voltammetric and UV/Vis spectroscopic recognition of Na+ and Ag+. Solution electrochemical studies reveal that metal complexation to the crown unit(s) leads to a significant positive shift in the potential of the first, two-electron oxidation wave of 9 and 12 [maximum shift E1ox = 115 mV for 9 in the presence of Ag+ (ca. 10 molar equivalents)]. Considerably smaller shifts (< 30 mV) were observed for complexation of Li+, K+ and Ba2+. UV/Vis spectrophotometric studies of metal binding (Na+ and Ag+) to 9 are consistent with the simultaneous formation of 1:1 and 1:2 complexes. The X-ray crystal structures of compounds 10 and 12-CH2Cl2 are reported. The anthracenediylidene moiety of 12 is U-shaped due to the boat conformation of the central (quinodimethane) ring and folding of both 1,3-dithiole rings, providing an overall saddle conformation. The folding in 10 is reduced as steric crowding is relieved by removal of one of the 1,3-dithiole units. © Wiley-VCH Verlag GmbH, 2001.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Bryce, MR
Batsanov, AS
Finn, T
Hansen, TK
Moore, AJ
Howard, JAK
Kamenjicki, M
Lednev, IK
Asher, SAasher@pitt.eduASHER
Date: 1 January 2001
Date Type: Publication
Journal or Publication Title: European Journal of Organic Chemistry
Number: 5
Page Range: 933 - 940
DOI or Unique Handle: 10.1002/1099-0690(200103)2001:5<933::aid-ejoc933<3.0.co;2-a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1434-193X
Date Deposited: 28 Mar 2013 16:22
Last Modified: 22 Jun 2021 13:55
URI: http://d-scholarship.pitt.edu/id/eprint/17814

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