Singh, Anil K. and Kishan, Ram and Bahadur, Vijay and Vijayan, Narayanasamy and Balachandran, Vadivelu and Tiwari, Hemandra K. and Singh, Brajendra K. and Rathi, Brijesh (2014) Synthesis, structural aspects and nonlinear optical properties of novel phthalimide derivatives: theoretical and experimental approach. Journal of Physical Organic Chemistry, 27 (6). pp. 490-497. ISSN 0894-3230

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Novel phthalimides (1, 2, 3) possessing variability of cyclic amines have been synthesized and characterized by analytical and spectroscopic techniques. Phthalimide 1 and 2 crystallized in a triclinic system with space group P; however, an orthorhombic system with a chiral space group of P2(1)2(1)2(1) was observed for 3 possessing piperidine cyclic amine. The hydrogen atoms attached to the central chiral carbon were oriented anti to each other resulting in minimum steric repulsion. The occurrence of C-H center dot center dot center dot O hydrogen bonds in 1, 2, 3 enabled the building of several supramolecular structures. Hyperpolarizability 197.6096 Debye angstrom(2) calculated for 1 was found to be higher than the hyperpolarizabilities, 138.0836 and 165.2521 Debye angstrom(2) measured for 2 and 3, respectively. Subsequently, phthalimides (1, 2, 3) were assessed for second harmonic generation (SHG) response, and a negligible response was recorded for 1 and 2; however, 3 showed a significant response of 14.2 mV. In addition to acentric structure, helical structural motifs identified in 3 could be responsible for its enhanced SHG response.

Item Type: Article
Additional Information: Copyright for this article belongs to M/S Wiley.
Uncontrolled Keywords: cyclic amine crystal structure hyperpolarizability phthalimide SHG response
Subjects: Chemistry
Depositing User: Dr. Rajpal Walke
Date Deposited: 23 Nov 2015 10:07
Last Modified: 23 Nov 2015 10:07

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