Functionalized organic frameworks explored as second order NLO agents

Abstract

Abstract.A new class of chiral phthalimides functionalized with aryl piperazines was designed anticipating their strong candidature for crystal engineering and technological applications. Five new phthalimides were synthesized, characterized and subjected to single crystal X-ray diffraction study that directed their noncentrosymmetric structures. Four phthalimides crystallized in P 2 1 space group with monoclinic crystal system, however, one was found to possess P 2 1 2 1 2 1 space group with orthorhombic system. The supramolecular architectures of phthalimide crystals were analysed by an approach based on consideration of energy of intermolecular interaction. The molecular hyperpolarizability (β) calculation for all the listed phthalimides indicated their promising candidature for NLO materials. Further, the crystalline form of all phthalimides was evaluated for their second harmonic generation (SHG) response. A significant response of 16.4 mV was measured for phthalimide possessing t-butyl substituent at the para position of 4-benzylpiperazine. This high SHG response may be attributed to the molecular chirality and helical supramolecular frameworks stabilized by C-H· · · O hydrogen bonds in the solid state. The current study attests chiral phthalimides possessing arylpiperazines as effective nominees to the area of crystal engineering and nonlinear optics.

Design, synthesis, and biological evaluation of new thalidomide–donepezil hybrids as neuroprotective agents targeting cholinesterases and neuroinflammation

“…Compounds 3a–h were obtained according to the methodology of Anil K. Singh and co-workers. 59 To a solution of N -phthaloylglycine (2.5 mmol) in dichloromethane (15 mL), N -(3-dimethylaminopropyl)- N′ -ethylcarbodiimide hydrochloride (EDC·HCl, 2.5 mmol) and triethylamine (TEA, 5.1 mmol) were added, and the reaction mixture was stirred at 0 °C for 15 min. Then, hydroxybenzotriazole (HOBT, 2.5 mmol) was added and the reaction mixture was stirred for an additional 15 min at 0 °C.…”

Design, synthesis and biological evaluation of Arylpiperazine-based novel Phthalimides: Active inducers of testicular germ cell apoptosis

“…Phthalimides (3a, 3e, 3g, 3i and 3m) have been previously prepared by our team and their structural aspects were investigated for nonlinear optical property. 37 All the compounds were characterized by spectroscopic tools and the corresponding spectroscopic data are described in supporting information.…”