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Phenylene-Diimine-Capped Conjugate of Lower Rim 1,3-Calix[4]Arene As Molecular Receptor for Mg2+ via Arm Conformational Changes Followed by Aggregation and Mimicking the Species by Molecular Mechanics

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Title Phenylene-Diimine-Capped Conjugate of Lower Rim 1,3-Calix[4]Arene As Molecular Receptor for Mg2+ via Arm Conformational Changes Followed by Aggregation and Mimicking the Species by Molecular Mechanics
 
Creator NEHRA, A
HINGE, VK
RAO, CP
 
Subject FLUORESCENT CHEMOSENSOR
MAGNESIUM
MOIETY
SENSOR
ZN2+
RECOGNITION
MODEL
 
Description A phenylene-diimine-capped conjugate of lower rim 1,3-calix[4]arene (L) was synthesized, characterized, and shown to selectively bind to Mg2+ using its capped arms. This results in a selective recognition of Mg2+ through eliciting fluorescence enhancement of similar to 70 fold with a detection limit of 40 +/- 5 ppb. However, in the presence of blood serum, the lowest detection limit is 209 +/- 10 ppb (0.2 mu M). The binding of Mg2+. to L is authenticated by absorption and H-1 NMR data. The Job's plot derived on the basis of the absorption data showed 1:1 stoichiometry between the receptor and Mg2+. The 1:1 species was further confirmed through ESI MS, that is, being supported by the isotope peak pattern authenticating the presence of Mg2+ in the complex. The L binds Mg2+ octahedrally using the tetradentate L2- and two additional acetic acid moieties by bringing conformational changes as studied on the basis of MM computations. The conformational changes that occur in the capped arms upon Mg2+ binding were supported experimentally by NOESY. AFM and SEM studies showed that spherical particles of L are modified into flower and chain type aggregates upon complexation with Mg2+, confirming the supramolecular behavior of the species formed.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-29T05:44:52Z
2014-12-29T05:44:52Z
2014
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 79(12)5763-5770
0022-3263
http://dx.doi.org/10.1021/jo500892r
http://dspace.library.iitb.ac.in/jspui/handle/100/17226
 
Language English