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Synthesis, Characterization, Crystal Structure, TGA and Blue Fluorescence of 6-(4-Chlorophenyl)-4-(4-methoxyphenyl)-2-methoxynicotinonitrile

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Abstract

6-(4-Chlorophenyl)-4-(4-methoxyphenyl)-2-methoxynicotinonitrile (1) was synthesized by cyclization reaction of a chalcone derivative and malononitrile and characterized by FT-IR, UV–Vis, 1H NMR and single crystal X-ray diffraction. The crystal of 1 belongs to monoclinic unit cell in the P21/c space group with the unit cell dimensions a = 3.8596(5) Å, b = 27.460(3) Å, c = 15.3972(19) Å, β = 99.115(3)o, V = 1611.3(3) Å3, Z = 4, D cald = 1.446 Mg m−3 and F(000) = 720. In addition, the thermal gravimetric analysis and fluorescent property of 1 were also carried out. The results reveal that 1 shows high thermal stability up to 300 °C and emit the strong blue fluorescence at 437 nm when was excited at 332 nm.

Graphical Abstract

6-(4-Chlorophenyl)-4-(4-methoxyphenyl)-2-methoxynicotinonitrile (1) was synthesized and characterized by spectroscopy methods and single X-ray diffraction. Compound 1 possesses blue fluorescence at the maxima emission wavelength 437 nm (excited at 332 nm) and the TGA data reveals that 1 shows thermal stability up to 300ºC.

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Acknowledgments

TS and SC thank the Thailand Research Fund through the Royal Golden Jubilee PhD Program (PHD/0257/2553) and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education, Ministry of Education, Thailand for financial support. The authors extend their appreciation to the Deanship of Scientific Research at the King Saud University, Saudi Arabia for funding the work through the research group Project No. RGP-VPP-207.

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Authors and Affiliations

  1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla, 90112, Thailand

    Thitipone Suwunwong & Suchada Chantrapromma

  2. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh, 11451, Saudi Arabia

    Hoong-Kun Fun

  3. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    Hoong-Kun Fun

Authors
  1. Thitipone Suwunwong
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  2. Suchada Chantrapromma
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  3. Hoong-Kun Fun
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Correspondence to Suchada Chantrapromma.

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Suwunwong, T., Chantrapromma, S. & Fun, HK. Synthesis, Characterization, Crystal Structure, TGA and Blue Fluorescence of 6-(4-Chlorophenyl)-4-(4-methoxyphenyl)-2-methoxynicotinonitrile. J Chem Crystallogr 43, 538–543 (2013). https://doi.org/10.1007/s10870-013-0454-6

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  • DOI: https://doi.org/10.1007/s10870-013-0454-6

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