A simple and efficient synthesis of a series of N-(thiazol-2-yl)piperidine-2,6-dione compounds and their interesting NLO properties

被引:0
|
作者
Shaiwale, Mayuri [1 ]
Som, Narayan N. [2 ,3 ]
Jha, Prafulla K. [2 ]
Ballabh, Amar [1 ]
机构
[1] Maharaja Sayajirao Univ Baroda, Fac Sci, Dept Chem, Vadodara 390002, Gujarat, India
[2] Maharaja Sayajirao Univ Baroda, Fac Sci, Dept Phys, Vadodara 390002, Gujarat, India
[3] Polish Acad Sci, Inst High Pressure Phys, Lab Nanostruct, Sokolowska 29-37, PL-01142 Warsaw, Poland
关键词
CENTER-DOT-O; NONLINEAR-OPTICAL PROPERTIES; GENERATION; SULFUR;
D O I
10.1039/d4ce00217b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A unique series of compounds was prepared from glutaric acid and various 2-amino thiazoles via a simple yet efficient synthetic method at ambient temperature. The N-(thiazol-2-yl)piperidine-2,6-dione derivatives were synthesized and characterized using multiple physicochemical techniques, X-ray crystallography, and SHG analysis. 2 out of the 5 newly synthesized compounds displayed strong nonlinear optical (NLO) properties. All five compounds were studied computationally, and UV spectroscopy was used to confirm the second harmonic generation (SHG) phenomenon. It was found that the compounds having a non-centrosymmetric space group have a larger band gap than the centrosymmetric space group and thus have more SHG properties. Compounds with large band gaps also have the distinctive S center dot center dot center dot O interaction, contributing significantly to conformational control of the crystal's geometry.
引用
收藏
页码:3069 / 3076
页数:8
相关论文
共 50 条
  • [31] Synthesis and in vitro antimicrobial activity of novel N-(6-chlorobenzo[d]thiazol-2-yl) hydrazine carboxamide derivatives of benzothiazole class
    Gilani, Sadaf J.
    Khan, Suroor A.
    Siddiqui, Nadeem
    Verma, Suraj P.
    Mullick, Pooja
    Alam, Ozair
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2011, 26 (03) : 332 - 340
  • [32] Synthesis, in Silico Study and Biological Evaluation of N-(Benzothiazol/Thiazol-2-yl)benzamide Derivatives as Quorum Sensing Inhibitors against Pseudomonas aeruginosa
    Sharma, Nikhil
    Srivastava, Namita
    Kaushal, Ashutosh
    Das, Bhanuranjan
    Vashistha, Aditi
    Kumar, Lokender
    Kumar, Rajnish
    Kumar Yadav, Ashok
    CHEMISTRY & BIODIVERSITY, 2023, 20 (09)
  • [33] N-(thiazol-2-yl)-2-thiophene carboxamide derivatives as Abl inhibitors identified by a pharmacophore-based database screening of commercially available compounds
    Manetti, Fabrizio
    Falchi, Federico
    Crespan, Emmanuele
    Schenone, Silvia
    Maga, Giovanni
    Botta, Maurizio
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (15) : 4328 - 4331
  • [34] Synthesis, pharmacological evaluation and docking studies of N-(benzo[d]thiazol-2-yl)-2-(piperazin-1-yl)acetamide analogs as COX-2 inhibitors
    Raghavendra, Nulgumnalli Manjunathaiah
    Jyothsna, Aitha
    Rao, Alapati Venkateswara
    Subrahmanyam, C. V. S.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) : 820 - 823
  • [35] Co(II) Complexes of4-((3-ethoxy-2-hydroxybenzylidene)amino)-N-(thiazol-2-yl)benzenesulphonamide and 4-((pyridin-2-ylmethylene)amino)-N-(thiazol-2-tl)benzenesulfonamide: Synthesis, Fluorescence Properties and Anticancer Activity
    Gomathi Vellaiswamy
    Selvameena Ramaswamy
    Journal of Fluorescence, 2017, 27 : 1559 - 1565
  • [36] Synthesis, structural, computational, electronic spectra, wave function properties and molecular docking studies of (Z)-4-(((5-methylfuran-2-yl) methylene)amino)-N-(thiazol-2-yl)benzenesulfonamide
    Thilagavathi, G.
    Kanagavalli, A.
    Jayachitra, R.
    Padmavathy, M.
    Elangovan, N.
    Thomas, Renjith
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2022, 99 (12)
  • [37] Co(II) Complexes of4-((3-ethoxy-2-hydroxybenzylidene)amino)-N-(thiazol-2-yl)benzenesulphonamide and 4-((pyridin-2-ylmethylene)amino)-N-(thiazol-2-tl)benzenesulfonamide: Synthesis, Fluorescence Properties and Anticancer Activity
    Vellaiswamy, Gomathi
    Ramaswamy, Selvameena
    JOURNAL OF FLUORESCENCE, 2017, 27 (05) : 1559 - 1565
  • [38] Synthesis, Crystal Structure and Fungicidal Activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl)propionamide
    Ye Jiao
    Sun Xiao-Xiao
    Qiu Shen-Yi
    Hu Ai-Xi
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33 (03) : 429 - 433
  • [39] Synthesis, characterization, computational, excited state properties, wave function, and molecular docking studies of (E)-4-((2-hydroxybenzylidene) amino)N-(thiazol-2-yl) benzenesulfonamide
    Kanagavalli, A.
    Jayachitra, R.
    Thilagavathi, G.
    Elangovan, N.
    Sowrirajan, S.
    Thomas, Renjith
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2023, 100 (02)
  • [40] Synthesis, Crystal Structure and Fungicidal Activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl)propionamide
    叶姣
    孙晓潇
    邱慎意
    胡艾希
    Chinese Journal of Structural Chemistry, 2014, (03) : 429 - 433