Octatosylaminophthalocyanine: A reusable chromogenic anion chemosensor

abstract

Detailed herein is the use of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine as a chromogenic chemosensor for anions. The host:guest complexes formed during the sensing event can be regenerated by acid treatment without loss of the sensing ability. This allows the phthalocyanine chemosensor to be reused. This system also responds in a colorimetric manner when exposed to the neutral solvent molecules, dimethyl sulfoxide and methanol. A single-crystal X-ray structure of the Pc 1:2 MeOH complex was obtained. It illustrates the main interactions between the host:guest species in the solid state. Fits of the binding curves are consistent with this stoichiometry predominating in the solution state. (C) 2014 Elsevier B.V. All rights reserved.

keywords

PORPHYRIN DERIVATIVES; RECEPTOR CHEMISTRY; BINDING PROPERTIES; AQUEOUS-MEDIA; SENSORS; HIGHLIGHTS; SUBPHTHALOCYANINE

subject category

Chemistry; Electrochemistry; Instruments & Instrumentation

authors

Farinha, ASF; Calvete, MJF; Paz, FAA; Tome, AC; Cavaleiro, JAS; Sessler, JL; Tome, JPC

our authors

acknowledgements

We would like to thank Fundacao para a Ciencia e a Tecnologia (FCT, Portugal), the European Union, QREN, COMPETE for funding the QOPNA (project PEst-C/QUI/UI0062/2013; FCOMP-01-0124-FEDER-037296) and CICECO (Pest C-CTM/LA0011/2013, FCOMP-01-0124-FEDER-037271) research units and the projects PTDC/CTM/101538/2008 and PPTDC/DG/QUI/82011/2006. We are further grateful for the financial support towards the purchase of the single-crystal diffractometer. A.S.F.F. also thanks FCT for her post-doc fellowship (SFRH/BPD/73060/2010). Thanks are also due

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