Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 7
158
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and nonlinear optical properties of pyridoxine-based stilbazole derivatives and their azo-analogs

, ORCID Icon, , , ORCID Icon, ORCID Icon, & show all
Pages 768-777 | Received 18 Sep 2017, Published online: 26 Feb 2018

References

  • Verbiest, T.; Houbrechts, S.; Kauranen, M.; Clays, K.; Persoons, A. Second-Order Nonlinear Optical Materials: Recent Advances in Chromophore Design. Phys. Rev. Lett. 1997, 7, 2175–2189. DOI: 10.1039/a703434b.
  • Cox, G. Biological Applications of Second Harmonic Imaging. Biophys. Rev. 2011, 3, 131–141. DOI: 10.1007/s12551-011-0052-9.
  • Chung, I.; Kanatzidis, G. M. Metal Chalcogenides: A Rich Source of Nonlinear Optical Materials. Chem. Mater. 2014, 26, 849–869. DOI: 10.1021/cm401737s.
  • Nath, G.; Haussuhl, S. Large Nonlinear Optical Coefficient and Phase- Matched Second Harmonic Generation in LiIO3. Appl. Phys. Lett. 1969, 14, 154–156. DOI: 10.1063/1.1652754.
  • Suresh, S.; Ramanand, A.; Jayaraman, D.; Mani, P. Review on Theoretical Aspect of Nonlinear Optics. Rev. Adv. Mater. Sci. 2012, 30, 175–183.
  • (a) Wang, A.; Yu, W.; Huang, Z.; Zhou, F.; Song, J.; Song, Y.; Long, L.; Cifuentes, M. P.; Humphrey, M. G.; Zhang, L.; et al. Covalent Functionalization of Reduced Graphene Oxide with Porphyrin by Means of Diazonium Chemistry for Nonlinear Optical Performance. Sci. Rep. 2016, 6, 1–12. DOI: 10.1038/srep23325; (b) Zhao, W.; Wang, A.; Wang, Y.; Lv, C.; Zhu, W.; Dou, S.; Wang, Q.; Zhong, Q. Accessible Fabrication and Mechanism Insight of Heterostructured BiOCl/Bi2MoO6/g-C3N4 Nanocomposites with Efficient Photosensitized Activity. J. Alloys Compd. 2017, 726, 164-172. DOI:10.1016/j.jallcom.2017.07.268; (c) Zhao, W.; Wang, Y.; Wang, A.; Qian, J.; Zhu, W.; Dou, S.; Wang, Q.; Zhong, Q.; Chen, A. Novel Bi2O2CO3/polypyrrole/g-C3N4 Nanocomposites With Efficient Photocatalytic and Nonlinear Optical Properties. RSC Adv. 2017, 7, 7658–7670.
  • (a) Le Bozec, H.; Renouard, T. Dipolar and Non-Dipolar Pyridine and Bipyridine Metal Complexes for Nonlinear Optics. Eur. J. Inorg. Chem. 2000, 2000, 229–239. DOI: 10.1002/(sici)1099-0682(200002)2000:2<229::aid-ejic229>3.0.co;2-a; (b) Cariati, E.; Pizzotti, M.; Roberto, D.; Tessore F.; Ugo, R. Coordination and Organometallic Compounds and Inorganic-Organic Hybrid Crystalline Materials for Second-Order Non-Linear Optics. Coord. Chem. Rev. 2006, 250, 1210–1233. DOI: 10.1016/j.ccr.2005.09.013; (c) Dragonetti, C.; Valore, A.; Colombo, A.; Righetto, S.; Rampinini, G.; Colombo, F.; Rocchigiani, L.; Macchioni, A. An Investigation on the Second-Order NLO Properties of Novel Cationic Cyclometallated Ir(III) Complexes of the Type [Ir(2-phenylpyridine)2(9-R-4,5-diazafluorene)]+ (R˭H, fulleridene) and the Related Neutral Complex with the New 9-Fulleriden-4-Monoazafluorene Ligand. Inorganica Chim. Acta. 2012, 382, 72-78. DOI: 10.1016/j.ica.2011.10.018; (d) Colombo, A.; Locatelli, D.; Roberto, D.; Tessore, F.; Ugo Righetto, S.; Rampinini, G.; Colombo, F.; Rocchigiani, L.; Macchioni, A. An Investigation on the Second-Order NLO Properties of Novel Cationic Cyclometallated Ir(III) Complexes of the Type [Ir(2-phenylpyridine)2(9-R-4,5-diazafluorene)]+ (R˭H, fulleridene) and the Related Neutral Complex with the New 9-Fulleriden-4-Monoazafluorene Ligand. Inorganica Chim. Acta. 2012, 382, 72-78. DOI: 10.1016/j.ica.2011.10.018; (d) Colombo, A.; Locatelli, D.; Roberto, D.; Tessore, F.; Ugo Uranyl-Organic One- and Two-Dimensional Assemblies with 2,2′-bipyridine-3,3′-dicarboxylic, biphenyl-3,3′,4,4′-tetracarboxylic and bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic Acids. Cryst. Eng. Comm. 2012, 14, 131-137. DOI: 10.1039/c1ce05772c.
  • Bourgogne, C.; Massona, P.; Nicouda, F.; Brasselet, S.; Zyss, J. Investigation of New Push–Pull Pyridine-1-Oxide Derivatives as 1D NLO Chromophores with Vanishing Dipole Moment. Synth. Met. 2001, 124, 213–216. DOI: 10.1016/s0379-6779(01)00453-2.
  • Pugachev, M. V.; Pavelyev, R. S.; Nguyen, T. N. T.; Iksanova, A. G.; Lodochnikova, O. A., Shtyrlin, Yu. G. Synthesis and Antitumor Activity of Pyridoxine Monoalkenyl Derivatives. Russ. Chem. Bull. 2016, 65, 532–536. DOI: 10.1007/s11172-016-1333-z.
  • (a) Marder, S. R.; Perry, J. W.; Schaefer, W. P. Synthesis of Organic Salts with Large Second-Order Optical Nonlinearities. Science 1989, 245, 626–628. DOI: 10.1126/science.245.4918.626; (b) Cole, J. M.; Edwards, T.-C.; Lin, A. J.; Piltz, R. O.; Depotter, G.; Clays, K.; Lee, S.-C.; Kwon, O.-P. Concerted Mitigation of O···H and C(π)···H Interactions Prospects Sixfold Gain in Optical Nonlinearity of Ionic Stilbazolium Derivatives. Appl. Mater. Interfaces. 2015, 7, 4693-4698. DOI: 10.1021/am508213c.
  • Kleinpeter, E.; Bölke, U.; Kreicberga, E. Quantification of the Pushe Pull Character of Azodyes and a Basis for Their Valuation as Potential Nonlinear Optical Materials. Tetrahedron 2010, 66, 4503–4509. DOI: 10.1016/j.tet.2010.04.067.
  • (a) Shtyrlin, Y. G.; Petukhov, A. S.; Strel’nik, A. D.; Garipov, M. R.; Lodochnikova, O. A.; Litvinov, I. A.; Morozov, O. A.; Lovchev, A. V. Derivatives of Pyridoxine with Nonlinear Optical Properties. RU Patent, 2501801, 2012; (b) Strel’nik, A. D.; Garipov, M. R.; Petukhov, A. S.; Shtyrlin, N. V.; Lodochnikova, O. A.; Litvinov, I. A.; Naumov, A. K.; Morozov, O. A.; Klimovitskii, A. E.; Shtyrlin, Y. G. Structural and Spectral Characterization of Novel Non-centrosymmetric 2,4-dinitrobenzene Derivative. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 2014, 117, 793–797.
  • Ziganshin, A. U.; Kalinina, O. S.; Strelnik, A. D.; Garipov, M. R.; Koshkin, S. A.; Ziganshina, L. E.; Shtyrlin, Y. G. Antagonistic Properties of New Non-Phosphorylated Derivatives of Nitrogen-Containing Heterocycles Towards P2 Receptors. Int. J. Pharmacol. 2015, 11, 400–404. DOI: 10.3923/ijp.2015.400.404.
  • Korytnyk, W. A Seven-Membered Cyclic Ketal of Pyridoxol. J. Org. Chem. 1962, 27, 3724–3726. DOI: 10.1021/jo01057a532.
  • (a) Shtyrlin, N. V.; Strel’nik, A. D.; Sysoeva, L. P.; Lodochnikova, O. A.; Klimovitskii, E. N.; Shtyrlin, Y. G. New Synthetic Method for 2,3,4-tris(hydroxymethyl)- 6-methylpyridin-5-ol. Russ. J. Org. Chem. 2009, 45, 1266–1268. DOI: 10.1002/chin.201009147; (b) Shtyrlin, N. V.; Lodochnikova, O. A.; Pugachev, M. V.; Madzhidov, T. I.; Sysoeva, L. P.; Litvinov, I. A.; Klimovitskii, E. N.; Shtyrlin, Y. G. Theoretical and Experimental Study on Cyclic 6-methyl-2,3,4-tris(hydroxymethyl)pyridin-5-ol acetonides. Russ. J. Org. Chem. 2010, 46, 561-567. DOI: 10.1134/s1070428010040202.
  • Shtyrlin, N. V.; Lodochnikova, O. A.; Shtyrlin, Y. G. Regioisomeric Oximes and Thiosemicarbazones Derived from 6-substituted Pyridoxines. Mendeleev Commun. 2012, 22, 169–170. DOI: 10.1016/j.mencom.2012.05.021.
  • Antonioletti, R.; Bonadies, F.; Ciammaichella, A.; Viglianti, A. Lithium Hydroxide as Base in the Wittig Reaction. A Simple Method for Olefin Synthesis. Tetrahedron 2008, 64, 4644–4648. DOI: 10.1016/j.tet.2008.02.091.
  • Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis; Wiley-VCH: Weinheim, 1999.
  • Katritzky, A. R.; Kucharska, H. Z.; Tucker, M. J.; Wuest, H. M. Arylazo Derivatives of Pyridoxine. J. Med. Chem. 1966, 9, 620–622. DOI: 10.1021/jm00322a046.
  • Huang, K.-S.; Britton, D.; Etter, M. C.; Byrnx, S. R. Synthesis, Polymorphic Characterization and Structural Comparisons of the Non-Linear Optically Active and Inactive Forms of Polymorphs of 3-(nitroanilino)cycloalk-2-en-1ones. J. Mater. Chem. 1996, 6, 123–129. DOI: 10.1039/jm9960600123.
  • Shemla, D.; Zyss, J. Nonlinear Optical Properties of Organic Molecules and Crystals; Academic Press: London, 1987.
  • Shtyrlin, Y. G.; Petukhov, A. S.; Strel’nik, A. D.; Nikitina, E. V.; Garipov, M. R. Antibacterial Compounds Based on Sulfanilic acid and Pyridoxine. RU Patent, 2480471, 2013.
  • Morozov, O. A.; Naumov, A. K.; Lovchev, A. V.; Garipov, M. R. Analysis of Nonlinear Optical Materials Properties by Simple Powder Technique. J. Phys. Conf. Ser. 2015, 594, 1–7. DOI: 10.1088/1742-6596/594/1/012037.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.