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Crystals 2018, 8(12), 467; https://doi.org/10.3390/cryst8120467

Crystal Structures and Optical Properties of Two Novel 1,3,5-Trisubstituted Pyrazoline Derivatives

1
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China
2
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China
*
Author to whom correspondence should be addressed.
Received: 18 November 2018 / Revised: 8 December 2018 / Accepted: 11 December 2018 / Published: 13 December 2018
(This article belongs to the Section Crystalline Materials)
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Abstract

Two novel 1,3,5-trisubstituted pyrazoline derivatives—1-acetyl-3-(4-methoxyphenyl)-5-(6-methoxy-2-naphthyl)-pyrazoline (2a) and 1-(4-nitrophenyl)-3-(4-methoxyphenyl)-5-(6-methoxy-2-naphtyl)-pyrazoline (2b)—were synthesized and their structures were determined by single crystal X-ray crystallography. Both of the two crystals exhibit twisted structures due to the large dihedral angles between the pyrazolinyl ring and the aromatic ring at the 5-position (88.09° for 2a and 71.26° for 2b). The optical–physical properties of the two compounds were investigated. The fluorescent emission of 2b arises from the 1,3-disubstituted pyrazoline chromophores and exhibits a red shift in polar solvents and solid-state, which could be attributed to photo-induced intramolecular charge transfer (ICT) from N1 to C3 in the pyrazoline moiety and the intermolecular interactions within the crystal. The fluorescent emissions of 2a (λmax 358–364 nm) in solvents and solid-state both come from 6-methoxy-2-naphthyl chromophores, which are fairly insensitive to the solvent polarity. View Full-Text
Keywords: pyrazoline derivatives; single crystal; fluorescence pyrazoline derivatives; single crystal; fluorescence
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Feng, Q.; Huan, W.; Wang, J.; Lu, J.; Diao, G.; Shan, Y. Crystal Structures and Optical Properties of Two Novel 1,3,5-Trisubstituted Pyrazoline Derivatives. Crystals 2018, 8, 467.

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