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Recognition of Polycyclic Aromatic Hydrocarbons and Their Derivatives by the 1,3-Dinaphthalimide Conjugate of Calix[4]arene: Emission, Absorption, Crystal Structures, and Computational Studies

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Title Recognition of Polycyclic Aromatic Hydrocarbons and Their Derivatives by the 1,3-Dinaphthalimide Conjugate of Calix[4]arene: Emission, Absorption, Crystal Structures, and Computational Studies
 
Creator BANDELA, A
CHINTA, JP
HINGE, VK
DIKUNDWAR, AG
ROW, TNG
RAO, CP
 
Subject MOLECULARLY IMPRINTED POLYMER
ENHANCED RAMAN-SCATTERING
LOWER RIM
SELECTIVE RECOGNITION
FLUORESCENCE DETECTION
AG NANOPARTICLES
PAHS
SENSOR
WATER
ZN2+
 
Description Polycyclic aromatic hydrocarbons (PAHs) are environmental pollutants as well as well-known carcinogens. Therefore, it is important to develop an effective receptor for the detection and quantification of such molecules in solution. In view of this, a 1,3-dinaphthalimide derivative of calix[4]arene (L) has been synthesized and characterized, and the structure has been established by single crystal XRD. In the crystal lattice, intermolecular arm-to-arm pi center dot center dot center dot pi overlap dominates and thus L becomes a promising receptor for providing interactions with the aromatic species in solution, which can be monitored by following the changes that occur in its fluorescence and absorption spectra. On the basis of the solution studies carried out with about 17 derivatives of the aromatic guest molecular systems, it may be concluded that the changes that occur in the fluorescence intensity seem to be proportional to the number of aromatic rings present and thus proportional to the extent of pi center dot center dot center dot pi interaction present between the naphthalimide moieties and the aromatic portion of the guest molecule. Though the nonaromatic portion of the guest species affects the fluorescence quenching, the trend is still based on the number of rings present in these. Four guest aldehydes are bound to L with K(ass) of 2000-6000 M(-1) and their minimum detection limit is in the range of 8-35 mu M. The crystal structure of a naphthaldehyde complex, L.2b, exhibits intermolecular arm-to-arm as well as arm-to-naphthaldehyde pi center dot center dot center dot pi interactions. Molecular dynamics studies of L carried out in the presence of aromatic aldehydes under vacuum as well as in acetonitrile resulted in exhibiting interactions observed in the solid state and hence the changes observed in the fluorescence and absorption spectra are attributable for such interactions. Complex formation has also been delineated through ESI MS studies. Thus L is a promising receptor that can recognize PAHs by providing spectral changes proportional to the aromatic conjugation of the guest and the extent of aromatic pi center dot center dot center dot pi interactions present between L and the guest.
 
Publisher AMER CHEMICAL SOC
 
Date 2012-06-26T08:56:45Z
2012-06-26T08:56:45Z
2011
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY,76(6)1742-1750
0022-3263
http://dx.doi.org/10.1021/jo1023409
http://dspace.library.iitb.ac.in/jspui/handle/100/14238
 
Language English