Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis, Crystal Structure, Luminescence, and Nonlinear Optical Properties of 2-[(E)-[[4-[2-(4-Methoxyphenyl)ethynyl]phenyl] imino]methyl]-4- [(E)-phenyldiazenyl]phenol

Author(s): Sagar Subhash Mohite, Aditya Babasaheb Patil-Deshmukh and Sanjay Shamrao Chavan*

Volume 17, Issue 8, 2020

Page: [618 - 623] Pages: 6

DOI: 10.2174/1570178617666200207104157

Price: $65

Abstract

2-((E)-((4-((4-methoxyphenyl)ethynyl)phenyl)imino)methyl-4-((E)phenyldiazenyl)phenol (1) have been synthesized and characterized. X-ray single crystal diffraction study of the compound 1 reveal a monoclinic structure. Room temperature luminescence is observed for 1 in CH2Cl2 solution due to π* → π transition. The SHG efficiency by Kurtz powder technique indicating the compound 1 displayed the second harmonic generation (SHG) property.

Keywords: NLO properties, photoluminescence, Schiff base, X-ray crystallography, NMR spectra, TGA.

Graphical Abstract
[1]
Shi, Q.; Xu, L.; Ji, J.; Li, Y.; Wang, R.; Zhou, Z.; Cao, R.; Hong, M.; Chan, A.S.C. Inorg. Chem. Commun., 2004, 7, 1254-1257.
[http://dx.doi.org/10.1016/j.inoche.2004.09.017]
[2]
Ye, X.; Chen, Y.; Ling, C.; Ding, R.; Wang, X.; Zhang, X.; Chen, S. Dalton Trans., 2018, 47(32), 10915-10924.
[http://dx.doi.org/10.1039/C8DT02278J] [PMID: 30046781]
[3]
Mohan, N.; Sreejith, S.S.; Begum, P.M.S.; Kurup, M.R.P. New J. Chem., 2018, 42, 13114-13121.
[http://dx.doi.org/10.1039/C8NJ02657B]
[4]
Vasanthi, B.J.; Ravikumar, L. Eur. Polym. J., 2007, 43, 4325-4331.
[http://dx.doi.org/10.1016/j.eurpolymj.2007.07.037]
[5]
Demitri, C.; De Benedictis, V.M.; Madaghiele, M.; Esposito Corcione, C.; Maffezzoli, A. Measurement, 2016, 90, 418-423.
[http://dx.doi.org/10.1016/j.measurement.2016.05.012]
[6]
Jarrahpour, A.A.; Motamedifar, M.; Pakshir, K.; Hadi, N.; Zarei, M. Molecules, 2004, 9(10), 815-824.
[http://dx.doi.org/10.3390/91000815] [PMID: 18007481]
[7]
Di Bella, S.; Oliveri, I.P.; Colombo, A.; Dragonetti, C.; Righetto, S.; Roberto, D. Dalton Trans., 2012, 41(23), 7013-7016.
[http://dx.doi.org/10.1039/c2dt30702b] [PMID: 22547326]
[8]
Oliveri, I.P.; Failla, S.; Malandrino, G.; Di Bella, S. New J. Chem., 2011, 35, 2826-2831.
[http://dx.doi.org/10.1039/c1nj20618d]
[9]
Zhou, L.; Cai, P.; Feng, Y.; Cheng, J.; Xiang, H.; Liu, J.; Wu, D.; Zhou, X. Anal. Chim. Acta, 2012, 735, 96-106.
[http://dx.doi.org/10.1016/j.aca.2012.05.022] [PMID: 22713922]
[10]
Consiglio, G.; Failla, S.; Finocchiaro, P.; Oliveri, I.P.; Di Bella, S. Dalton Trans., 2012, 41(2), 387-395.
[http://dx.doi.org/10.1039/C1DT11295C] [PMID: 22005842]
[11]
Hai, Y.; Chen, J-J.; Zhao, P.; Lv, H.; Yu, Y.; Xu, P.; Zhang, J-L. Chem. Commun. (Camb.), 2011, 47(8), 2435-2437.
[http://dx.doi.org/10.1039/C0CC04113K] [PMID: 21170447]
[12]
Yam, W.V.W.; Wo, K.K.; Wing, Lo.; Wong, K.M. J. Organomet. Chem., 1999, 578, 3-30.
[http://dx.doi.org/10.1016/S0022-328X(98)01106-1]
[13]
Ma, C.; Lo, A.; Abdolmaleki, A.; MacLachlan, M.J. Org. Lett., 2004, 6(21), 3841-3844.
[http://dx.doi.org/10.1021/ol0483549] [PMID: 15469363]
[14]
More, M.S.; Devkule, S.S.; Chavan, S.S. Inorg. J. Fluorese., 2017, 27, 841-851.
[http://dx.doi.org/10.1007/s10895-016-2020-z]
[15]
Liu, J-n.; Wu, B-w.; Zhang, B.; Liu, Y. Turk. J. Chem., 2006, 30, 41-48.
[16]
Sheldrick, G.M. Acta Crystallogr. A, 2008, 64(Pt 1), 112-122.
[http://dx.doi.org/10.1107/S0108767307043930] [PMID: 18156677]
[17]
Lavastre, O. Vohlidal., 1997, 53, 7064-7595.
[18]
Sarigul, M.; Sari, A.; Kose, M.; McKee, V.; Elmastas, M.; Demirtas, I.; Kurtoglu, M. Inorg. Chim. Acta, 2016, 444, 166-175.
[http://dx.doi.org/10.1016/j.ica.2016.01.042]
[19]
Alaghaz, A-N.M.A.; Ammar, Y.A.; Bayoumi, H.A.; Aldhlmani, S.A. J. Mol. Struct., 2014, 1074, 359-375.
[http://dx.doi.org/10.1016/j.molstruc.2014.05.078]
[20]
Azam, M.; Hussain, Z.; Warad, I.; Al-Resayes, S.I. Dalton Trans., 2012, 41, 10854-10864.
[http://dx.doi.org/10.1039/c2dt31143g] [PMID: 22858862]
[21]
Mohite, S.S.; Patil-Deshmukh, A.B.; Chavan, S.S. J. Mol. Struct., 2019, 1176, 386-393.
[http://dx.doi.org/10.1016/j.molstruc.2018.08.085]
[22]
Dal, H.; Suezen, Y.; Sahin, E. Spectrochim. Acta., 2007, 67A, 808-814.
[http://dx.doi.org/10.1016/j.saa.2006.08.037]
[23]
Ikiz, M.; Ispir, E.; Aytar, E.; Ulusoy, M.; Karabug, S.; Aslantas, M.; Celik, O. New J. Chem., 2015, 39, 7786-7796.
[http://dx.doi.org/10.1039/C5NJ00571J]
[24]
Ziessel, R.; Suffert, J.; Youinou, M-T. J. Org. Chem., 1996, 61(19), 6535-6546.
[http://dx.doi.org/10.1021/jo960538g] [PMID: 11667517]
[25]
Jee, J-E.; Kim, Y-M.; Lee, S.S.; Park, K-M.; Kwak, C-H. Inorg. Chem. Commun., 2003, 6, 946-949.
[http://dx.doi.org/10.1016/S1387-7003(03)00157-6]
[26]
Zyss, J.; Ledoux, L. Chem. Rev., 1994, 94, 77-105.
[http://dx.doi.org/10.1021/cr00025a003]
[27]
Di Bella, S. Chem. Soc. Rev., 2001, 30, 355-366.
[http://dx.doi.org/10.1039/b100820j]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy