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Effect of substituents on crystal packing of functionalized 4,4 '-bis(benzylideneamino)diphenyl ether(s) and their reduced benzyl forms: Synthesis, characterization, optical and thermal properties

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Title Effect of substituents on crystal packing of functionalized 4,4 '-bis(benzylideneamino)diphenyl ether(s) and their reduced benzyl forms: Synthesis, characterization, optical and thermal properties
 
Creator KADU, R
SINGH, VK
VERMA, SK
RAGHAVAIAH, P
SHAIKH, MM
 
Subject Organic compounds
Crystal engineering
Non-covalent interactions
Optical properties
Thermal behavior
O HYDROGEN-BONDS
DOT-N INTERACTIONS
PI-PI INTERACTIONS
C-H
SOLID-STATE
CH/PI INTERACTION
AMORPHOUS-SEMICONDUCTORS
MOLECULAR RECOGNITION
AROMATIC INTERACTIONS
SECONDARY-AMINES
 
Description In this paper we report the synthesis of 4,4'-bis(benzylideneamino)diphenyl ether (1), 4,4'-bis(p-methoxybenzylideneamino)diphenyl ether (2), 4,4'-bis(p-nitrobenzylideneamino)diphenyl ether (3), 4,4'-bis(benzylamino)diphenyl ether (4) and 4,4'-bis(p-methoxybenzylamino)diphenyl ether (5). The new compounds were characterized by using standard spectroscopic techniques. Supramolecular structures of 1-4 have been studied by using single-crystal X-ray diffraction to gauge the influence of substituents, present on para-positions of peripheral phenyl rings, on the association of molecules in the solid state. The study showed that introduction of p-OCH3 and p-NO2 substituents on peripheral phenyl rings, successfully switches off CH center dot center dot center dot pi synthons seen in compound 1 and 4 and that the new compounds adopt other packing strategies based on CH center dot center dot center dot O (2) and CH center dot center dot center dot N, CH center dot center dot center dot O and pi center dot center dot center dot pi (3) interactions. The optical band gaps (Eg), calculated by optical absorption method fall in the range of 2.16-3.0 eV and demonstrate a wide band gap semiconducting nature of these compounds. The thermogravimetric study of these compounds suggests the total destruction of the molecules up to 550 degrees C with a remaining mass of
 
Publisher ELSEVIER SCIENCE BV
 
Date 2014-10-16T12:16:34Z
2014-10-16T12:16:34Z
2013
 
Type Article
 
Identifier JOURNAL OF MOLECULAR STRUCTURE, 1033298-311
0022-2860
1872-8014
http://dx.doi.org/10.1016/j.molstruc.2012.10.041
http://dspace.library.iitb.ac.in/jspui/handle/100/15523
 
Language en