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Synthesis, characterization, X-ray structure, optical properties and theoretical calculations of condensed phthalazines

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Abstract

Two condensed phthalazine compounds were synthesized and characterized by FT-IR, UV-Vis, NMR spectroscopic studies. Single crystal XRD and molecular orbital calculations. Optimized geometrical structures were computed with RB3LYP method with the 6-31G(p, d) basis set. The geometrical parameters of both compounds obtained from Single Crystal XRD were found to be in accord with the calculated (DFT) values. The electronic contribution \(\chi _{THG}^{<3>} \) was measured using the third harmonic generation technique on thin films at 1064 nm for both compounds. Also, the values of dipole moment \(\upmu \), the average polarizability \({\bar{\upalpha }}\), and the first static hyperpolarizability \(\left( {\beta _0 } \right) \) were computed. The theoretical and experimental results confirm the NLO behavior of both compounds.

Graphical Abstract

SYNOPSIS Two condensed phthalazine compounds were synthesized and characterized by IR, UV-Vis, NMR spectroscopy and Single Crystal XRD. The geometrical parameters of both the compounds obtained from XRD studies are in accordance with the calculated values. Their electronic contributions \(\chi _{THG}^{<3>} \) have been measured using the third harmonic generation technique on thin films at 1064 nm.

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References

  1. Xue D Q, Zhang X Y, Wang C J, Ma L Y, Zhu N, He P, Shao K P, Chen P J, Gu Y F, Zhang X S, Wang C F, Ji C H, Zhang QR and Liu H M 2014 Synthesis and anticancer activities of novel 1,2,4-triazolo[3,4-a]phthalazine derivatives Eur. J. Med. Chem. 85 235

    Article  CAS  Google Scholar 

  2. Zhang Q R, Xue D Q, He P, Shao K P, Chen P J, Gu Y F, Ren J L, Shan L H and Liu H M 2014 Synthesis and antimicrobial activities of novel 1,2,4-triazolo [3,4-a] phthalazine derivatives Bioorg. Med. Chem. Lett. 24 1236

    Article  CAS  Google Scholar 

  3. Ryu C K, Park R E, Ma M Y and Nho J H 2007 Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones Bioorg. Med. Chem. Lett. 17 2577

    Article  CAS  Google Scholar 

  4. Sinkkonen J, Ovcharenko V, Zelenin K N, Bezhan I P, Chakchir B A, Al-Assar F and Pihlaja K 2002 \(^{1}\text{H }\)]phthalazine-5,10-diones and Their Ring-Chain Tautomerism Eur. J. Org. Chem. 2002 2046

    Article  Google Scholar 

  5. Sangani C B, Makwana J A, Duan Y T, Thumar N J, Zhao M Y, Patel Y S and Zhu H L 2016 Synthesis of 1\(H\)-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: Assessment of their antimicrobial, antituberculosis and antioxidant activity Res. Chem. Intermed. 42 2101

    Article  CAS  Google Scholar 

  6. Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K and Adachi H 1998 4-Benzylamino-1-chloro-6-substituted phthalazines: Synthesis and inhibitory activity toward phosphodiesterase 5 J. Med. Chem. 41 3367

    Article  CAS  Google Scholar 

  7. Wu H, Chen X M, Wan Y, Xin H Q, Xu H H, Ma R, Yue C H and Pang L L 2009 Synthesis and Luminescence of 7-amino-2H-indazolo[2,1-b]phthalazine- 1,6,11(13H)-triones Catalyzed by Silica Sulfuric Acid Lett. Org. Chem. 6 219

    Article  CAS  Google Scholar 

  8. Prasad P N and Williams D J 1991 In Introduction to nonlinear optical effects in molecules and Polymers (New York: Wiley) pp. 120–131

  9. Ekbote A, Patil P S, Maidur S R, Chia T S and Quah C K 2017 Structure and nonlinear optical properties of (E)-1-(4-aminophenyl)-3-(3-chlorophenyl) prop-2-en-1-one: A promising new D-\(\pi \)-D type chalcone derivative crystal for nonlinear optical devices J. Mol. Struct. 1129 239

    Article  CAS  Google Scholar 

  10. Morales A R, Frazer A, Woodward A W, Ahn-White H -Y, Fonari A, Tongwa P, Timofeeva T and Belfield K D 2013 Design, Synthesis, and Structural and Spectroscopic Studies of Push–Pull Two-Photon Absorbing Chromophores with Acceptor Groups of Varying Strength J. Org. Chem. 78 1014

    Article  CAS  Google Scholar 

  11. Ramkumar V, Anandhi S, Kannan P and Gopalakrishnan R 2013 Synthesis, single crystal growth, characterization and comparison of two new enone shifted chalcones and their NLO behavior CrystEngComm 15 2438

  12. Arroudj S, Bouchouit M, Bouchouit K, Bouraiou A, Messaadia L, Kulyk B, Figa V, Bouacida S, Sofiani Z and Taboukhat S 2016 Synthesis, spectral, optical properties and theoretical calculations on schiff bases ligands containing o-tolidine Opt. Mater. 56 116

    Article  CAS  Google Scholar 

  13. Bouchouit M, Elkouari Y, Messaadia L, Bouraiou A, Arroudj S, Bouacida S, Taboukhat S and Bouchouit K 2016 Synthesis, spectral, theoretical calculations and optical properties performance of substituted-azobenzene dyes Opt. Quant. Electron. 48 178

    Article  Google Scholar 

  14. Nabid M R, Rezaei S J T, Ghahremanzadeh R and Bazgir A 2010 Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones Ultrason. Sonochem. 17 159

    Article  CAS  Google Scholar 

  15. Safaei-Ghomi J, Shahbazi-Alavi H, Ziarati A, Teymuri R and Saberi M R 2014 A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with CuI nanoparticles as catalyst under solvent-free conditions Chin. Chem. Lett. 25 401

    Article  CAS  Google Scholar 

  16. Khurana J M and Magoo D 2009 Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic \(\text{H }_{2}\text{SO }_{4}\) in water–ethanol or ionic liquid Tetrahedron Lett. 50 7300

    Article  CAS  Google Scholar 

  17. Atar A B, Lee S D, Cho B G, Cho D W and Jeong Y T 2016 \(\beta \): the most efficient catalyst for one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions Res. Chem. Intermed. 42 1707

    Article  CAS  Google Scholar 

  18. Burla M C, Caliandro R, Camalli M, Carrozzini B, Cascarano G L, De Caro L, Giacovazzo C, Polidori G and Spagna R 2005 an improved tool for crystal structure determination and refinement J. Appl. Cryst. 38 381

    Article  CAS  Google Scholar 

  19. Sheldrick G M 2008 A short history of SHELX Acta Cryst. A 64 112

    Article  CAS  Google Scholar 

  20. Farrugia L J 2012 WinGX and ORTEP for Windows: An update J. Appl. Cryst. 45 849

    Article  CAS  Google Scholar 

  21. Sheldrick G M 2002 SADABS Bruker AXS Inc., Madison, Wisconsin, USA

  22. Maker D, Terhune R W, Niseno M F and Savage C M 1962 Effects of Dispersion and Focusing on the Production of Optical Harmonics Phys. Rev. Lett. 8 21

    Article  Google Scholar 

  23. Dennington R, Keith T and Millam J 2009 GaussView Version 5.0.9, Semichem Inc.: Shawnee Mission KS

  24. Becke A D 1988 Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 38 3098

    Article  CAS  Google Scholar 

  25. Perdew J P 1986 Density-functional approximation for the correlation energy of the inhomogeneous electron gas Phys. Rev. B 33 8822

    Article  CAS  Google Scholar 

  26. Gubler U and Bosshard C 2000 Optical third-harmonic generation of fused silica in gas atmosphere: Absolute value of the third-order nonlinear optical susceptibility \(\chi ^{(3)}\) Phys. Rev. B 61 10702

    Article  CAS  Google Scholar 

  27. Kubodera K and Kobayashi H 1990 Determination of Third-Order Nonlinear Optical Susceptibilities for Organic Materials by Third-Harmonic Generation Mol. Cryst. Liq. Cryst. 182 103

    Google Scholar 

  28. Fleming I 1976 Frontier Orbitals and Organic Chemical Reactions (New York: John Wiley) pp. 05–27

  29. Zhang C R, Chen H S and Wang G H 2004 Structure and properties of semiconductor microclusters GanPn (n= 1-4): a first principle study Chem. Res. Chin. U. 20 640

    CAS  Google Scholar 

  30. Sun Y, Chen X, Sun L, Guo X and Lu W 2003 Nanoring structure and optical properties of \(\text{Ga }_{8}\text{ As }_{8}\) Chem. Phys. Lett. 397

  31. Kleinman, D A 1962 Nonlinear Dielectric Polarization in optical media Phys. Rev. 126 1977

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the Ministère de l’Enseignement Supérieur et de la Recherche Scientifique—Algérie (MESRS) for financial support. AB thanks Professor H. Merazig (UR. CHEMS, Université des Frères Mentouri, Constantine) for his assistance in structural determination.

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Authors and Affiliations

  1. Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Université des Frères Mentouri, Constantine, 25000, Algeria

    Esma Lamera, Sofiane Bouacida, Aissa Chibani & Abdelmalek Bouraiou

  2. Laboratoire Énergétique Appliquée et Matériaux, Université de Jijel, 18000, Jijel, Algeria

    Lyamine Messaadia

  3. Département des sciences de la matière, Université Oum El Bouaghi, 04000, Oum El Bouaghi, Algeria

    Sofiane Bouacida

  4. Ecole Normal Supérieure de Constantine, Ville Universitaire, Ain El Bey Ali Mendjeli, Constantine, Algeria

    Karim Bouchouit

  5. CNRS UMR 6200, Laboratoire MOLTECH-Anjou, LUNAM Université, Université d’Angers, 2 Bd Lavoisier, 49045, Angers Cedex, France

    Bouchta Sahraoui

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  1. Esma Lamera
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  2. Lyamine Messaadia
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  7. Abdelmalek Bouraiou
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Correspondence to Abdelmalek Bouraiou.

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Lamera, E., Messaadia, L., Bouacida, S. et al. Synthesis, characterization, X-ray structure, optical properties and theoretical calculations of condensed phthalazines. J Chem Sci 129, 721–731 (2017). https://doi.org/10.1007/s12039-017-1278-2

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  • DOI: https://doi.org/10.1007/s12039-017-1278-2

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