Investigation of Spectroscopic Behaviors of Newly Synthesized (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one (DDTP) Dye
详细信息    查看全文
  • 作者:Abdullah M. Asiri (1) (2)
    Hadi M. Marwani (1) (2)
    Salman A. Khan (1)
    Samy A. El-Daly (1) (3)
  • 关键词:DDTP ; Stoichiometric ratios ; Physicochemical parameters ; Fluorescence ; Photostability
  • 刊名:Journal of Fluorescence
  • 出版年:2013
  • 出版时间:November 2013
  • 年:2013
  • 卷:23
  • 期:6
  • 页码:1271-1278
  • 全文大小:298KB
  • 参考文献:1. Asiri AM, Khan SA (2011) Synthesis, characterization and optical properties of mono- and bis-chalcone. Mater Lett 65:1749鈥?752 CrossRef
    2. Menger FM, Smith JH (1969) Kinetics and mechanism of reactions of cis-and trans-chalcones with amines. J Am Chem Soc 91:4211鈥?216 CrossRef
    3. Gularian SK, Dobretsov GE (2003) Svetlichny沫 VIu. [Fluorescent probe 4-dimethylaminochalcone: mechanism of fluorescence quenching in nonpolar media]. Biofizika 48(5):873鈥?79
    4. Pant GJ, Singh P, Rawat BS, Rawat MSM, Joshi GC (2011) Synthesis, characterization and fluorescence studies of 3,5-diaryl substituted 2-pyrazolines. Spectrochim Acta Part A: Mol Biomol Spectrosc 78:1075鈥?079 CrossRef
    5. Osman SA, Yosef HAA, Hafez TS, El-Sawy AA, Mousa HA, Ashraf S, Hassan AS (2012) Synthesis and antibacterial activity of some novel chalcones, pyrazoline and 3-cyanopyridine derivatives based on khellinone as well as Ni(II), Co(II) and Zn(II) Complexes. Aust J Basic Appl Sci 6(3):852鈥?63
    6. Shah SNN, Ziauddin HM, Zameer M, Hingole SS, Baseer MA (2010) An introduction of some novel pyrazolines to synthetic chemistry and antimicrobial studies. J Chem Pharm Res 2(6):441鈥?45
    7. Lee SK, Cho MJ, Jin J, Choi DH (2007) Polarized-light-induced enhancement of the electro-optic properties in a photoreactive maleimide copolymer. J Korean Phy Soc 51:1668鈥?672 CrossRef
    8. Jaung J, Matsuoka M, Fukunishi K (1999) Dicyanopyrazine studies. Part V: syntheses and characteristics of chalcone analogues of dicyanopyrazine. Dye Pigment 40:11鈥?0 CrossRef
    9. Stefanisinova M, Tomeckova V, Kozurkova M, Ostro A, Marekova M (2011) Study of DNA interactions with cyclic chalcone derivatives by spectroscopic techniques. Spectrochim Acta Part A: Mol Biomol Spectrosc 81:666鈥?71 CrossRef
    10. Perumal R, Ayyavu T, Sebastian R, Shanmugam G, Pichai M (2012) Photophysical properties and dye-sensitized solar cell studies on thiadiazole-triazole-chalcone dendrimers. Tet Lett 53:1129鈥?132
    11. Shettigar S, Umesh G, Chandrasekharan K, Sarojini BK, Narayana B (2008) Studies on third-order nonlinear optical properties of chalcone derivatives in polymer host. Opt Mater 30:1297鈥?303 CrossRef
    12. Jung YJ, Son K, Oh YE, Noh D (2008) Ferrocenyl chalcone containing anthracenyl group: synthesis, X-ray crystal structures and electrochemical properties. Polyhedron 27:861鈥?67 CrossRef
    13. Kumar PCR, Ravindrachary V, Janardhana K, Manjunath HR, Karegouda P, Crasta V, Sridhar MA (2011) Optical and structural properties of chalcone NLO single crystals. J Mol Struct 1005:1鈥? CrossRef
    14. Asiri AM, Khan SA (2011) Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products. Molecules 16:523鈥?31 CrossRef
    15. Ratkovic Z, Juranic ZD, Stanojkovic T, Manojlovic D, Vukicevic RD, Radulovic N, Joksovic MD (2010) Synthesis, characterization, electrochemical studies and antitumor activity of some new chalcone analogues containing ferrocenyl pyrazole moiety. Bioorg Chem 38:26鈥?2 CrossRef
    16. Arancibia R, Biot C, Delaney G, Roussel P, Pascual A, Pradines B, Klahn AH (2013) Cyrhetrenyl chalcones: synthesis, characterization and antimalarial evaluation. J Organomet Chem 723:143鈥?48 CrossRef
    17. Manna K, Agrawal YK (2009) Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity. Bioorg Med Chem Lett 19:2688鈥?692 CrossRef
    18. Marwani HM, Asiri AM, Khan SA (2013) Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media. J Lumin 136:298鈥?02 CrossRef
    19. Rathod AK, Kulkarni GB (2011) Synthesis of 2-mercapto-dihydropyrimidines derivatives under conventional and microwave digestion technique and their anti-cancer and anti-tuberculosis activity. Int J Pharm Tech Res 3:728鈥?31
    20. Asiri AM, Marwani HM, Khan SA (2011) Spectroscopic investigation of novel donor鈥揳cceptor chromophores as specific application agents for opto-electronics and photonic. J Saudi Chem Soc. doi:10.1016/j.jscs.2011.08.003
    21. Marwani HM, Asiri AM, Khan SA (2012) Green-synthesis, characterization, photostability and polarity studies of novel Schiff base dyes using spectroscopic methods. Russ J Bioorg Chem 38:533鈥?38 CrossRef
    22. Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Kluwer Academic/Plenum Press, New York CrossRef
    23. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703鈥?707 CrossRef
    24. Brannon JH, Magde D (1978) Absolute quantum yield determination by thermal blooming: fluorescein. J Phys Chem 82(6):705鈥?09 CrossRef
    25. Fery-Forgues S, Lavabre D (1999) Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationery products. J Chem Educ 76:1260鈥?264 CrossRef
    26. Lippert E (1957) Spectroscopic determinations of the dipole moment of aromatic compounds in the first excited singlet state. Z Electrochem 61:962鈥?75
    27. Turro NJ (1965) Molecular photochemistry (frontiers in chemestry), 1st ed., W. A. Benjamin, Inc., Reading, MA p 286
    28. Coe BJ, Harris JA, Asselberghs I, Clays K, Olbrechts G, Persoons A, Hupp JT, Johnson RC, Coles SJ, Hursthouse MB, Nakatani K (2002) Quadratic nonlinear optical properties of n-aryl stilbazolium dyes. Adv Funct Mater 12:110鈥?16 CrossRef
    29. Kumar S, Rao VC, Rastogi RC (2001) Excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, ET N. Spectrochim Acta Part A 57:41鈥?7 CrossRef
    30. Ravi M, Soujanya T, Samanta A, Radhakrishnan TP (1995) Excited-state dipole moments of some coumarin dyes from a solvatochromic method using the solvent polarity parameter, ET N. J Chem Soc Faraday Trans 91:2739鈥?742 CrossRef
  • 作者单位:Abdullah M. Asiri (1) (2)
    Hadi M. Marwani (1) (2)
    Salman A. Khan (1)
    Samy A. El-Daly (1) (3)

    1. Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, Saudi Arabia, 21589
    2. Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah, Saudi Arabia, 21589
    3. Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt
  • ISSN:1573-4994
文摘
This study introduced spectroscopic properties, physicochemical parameters, and polarity and photostability behaviors of a newly prepared chalcone dye. The chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one (DDTP), was synthesized by the reaction of 3,4-dimethoxybenzaldehyde with 3-acetyl-2,5-dimethythiophene. Results of FT-IR, 1H-NMR, 13C-NMR and elemental analysis were in conformity with chemical structure of newly prepared DDTP. Data of thermal gravimetric analysis revealed that DDTP has good thermal stability. Increases in fluorescence intensities of DDTP with cetyltrimethyl ammonium bromide (CTAB) were observed. In comparison of fluorescence intensities for DDTP with CTAB, reductions in fluorescence intensities for DDTP with sodium dodecyl sulphate (SDS) were observed under the same experimental and instrumental conditions. Moreover, Benesi-Hildebrand method was applied to determine stoichiometric ratios and association constants of DDTP with CTAB and SDS. The stoichiometric ratio and association constant obtained from Stern-Volmer plot strongly supported those obtained from Benesi-Hildebrand plot of DDTP with SDS. Physicochemical parameters, such as, singlet absorption, molar absorptivity, oscillator strength, dipole moment and fluorescence quantum yield of DDTP were also estimated. Fluorescence steady-state measurements ultimately displayed that DDTP has a high photostability against photobleaching. Fluorescence polarity study revealed that DDTP was sensitive to the polarity of the microenvironment provided by different solvents.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700