eprintid: 17814
rev_number: 31
userid: 1419
dir: disk0/00/01/78/14
datestamp: 2013-03-28 16:22:33
lastmod: 2021-06-12 23:55:34
status_changed: 2013-03-28 16:22:33
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Bryce, MR
creators_name: Batsanov, AS
creators_name: Finn, T
creators_name: Hansen, TK
creators_name: Moore, AJ
creators_name: Howard, JAK
creators_name: Kamenjicki, M
creators_name: Lednev, IK
creators_name: Asher, SA
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creators_email: asher@pitt.edu
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creators_id: ASHER
title: 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
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2001-01-01
date_type: published
publication: European Journal of Organic Chemistry
number: 5
pagerange: 933 - 940
refereed: TRUE
issn: 1434-193X
id_number: 10.1002/1099-0690(200103)2001:5<933::AID-EJOC933<3.0.CO;2-A
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/17814/1/licence.txt