Solvent Effect on the Fluorescence Properties of Two Biologically Active Thiophene Carboxamido Molecules

Authors

  • D Nagaraja Department of Physics, Bangalore Institute of Technology, Bangalore-560004, Karnataka, India
  • H S Geethanjali Department of Physics, Bangalore Institute of Technology, Bangalore-560004, Karnataka, India
  • N R Patil Department of Physics, B V B College of Engineering and Technology, Hubli-580031, Karnataka, India
  • F M Sanningannavar Department of Physics, Karnatak Science College Dharwad-580003, Karnataka, India
  • R A Kusanur Department of Chemistry, R. V. College of Engineering, Bangalore-560059, Karnataka, India
  • R M Melavanki Department of Physics, M S Ramaiah Institute of Technology Bangalore-560054, Karnataka, India

DOI:

https://doi.org/10.12723/mjs.24.6

Keywords:

Solvatochromic shift method, Ground state dipole moments, Excited state dipole moments, Thiophene carboxamido.

Abstract

The absorption and fluorescence spectra of two thiophene carboxamido molecules namely 2–( - trimethoxy phenyl) imino–3–N–ethylcarboxamido–4, 5, tetramethylene thiophene (X) and 2-( -N, N-dimethylaminophenyl) imino-3-(N- methylphenyl carboxamido)-4, 5, tetramethylene thiophene (Y) have been recorded at room temperature. The ground (mg) and excited (me) state dipole moments are estimated from Lippert, Bakhshiev, Kawski-Chamma-Viallet equations by using the variation of Stokes shift with microscopic solvent dielectric constant (e) and refractive index (n). The excited dipole moments were also estimated by using the variation of Stokes shift with microscopic empirical solvent polarity parameter and the values are compared. It was estimated that dipole moments of the excited state were higher than those of the ground state of both the molecules. Further, the change in dipole moment (Dm) were calculated both from solvatochromic shift method and on the basis of microscopic empirical solvent polarity parameter .

References

K. K. Rothatgi-Mukherjee, Fundamental of Photochemistry, Wiley Easten Ltd., New Delhi, India, 1986.

J. R. Lackowicz, Principles of Fluorescence Spectroscopy, Plenum Press New York, 1983.

J. R. Sheats and P. F. Barbara, “Molecular Materials in electronic and optoelectronic devices,”Acc. Chem. Res., vol. 32, p. 191, 1999.

K. H. Drexhage in: F. P. Schafer, Structure and Properties of Laser Dyes, Topics in Applied Physics, Springer-Verlag, Berlin, p. 143, 1973.

D. Binder, C. R. Noe, W. Holzer and B. Rosenworth, “Thiophen als Strukturelement physiologisch aktiver Substanzen, 12. Mitt. Thiophenanaloga antiviraler Chalkone,” Arch. de Pharm. vol. 318,

p. 48, 1985. http://dx.doi.org/10.1002/ardp.19853180111.

G. Karminshi–Aamola and M. Bajc, “Synthesis of (5-Styryl-2-thienyl)-phenylacrylic Acids,” Heterocycles, vol. 23, p. 1497, 1985. http:// dx.doi.org/10.3987/R-1985-06-1497.

C. Richards, Solvents and Solvent Effects in Organic Chemistry, VCH, New York, 1991.

B. Koutek, “Dipole moments in excited state. Statistical investigation of methods employing solvatochromism,” Collect. Czech. Chem. Commun., vol. 43, p. 2368, 1978. http://dx.doi.org/ 10.1135/ cccc19782368.

N. R. Patil, R. M. Melavanki, S. B. Kapatkar, N. H. Ayachit and J. Saravanan, “Solvent Effect on Absorption and Fluorescence Spectra of Three Biologically Active Carboxamides (C1, C2 and C3). Estimation of Ground and Excited State Dipole Moment from Solvatochromic Method Using Solvent Polarity Parameters”, J. Fluoresc., vol. 21,

p. 1213, 2011. http://dx.doi.org/ 10.1007/s10895-010-0800-4.

R. M. Melavanki, N. R. Patil, S. B. Kapatkar, N. H. Ayachit, S. Umapathy, J Thipperudrappa and A R Nataraju, “Solvent effect on the spectroscopic properties of 6MAMC and 7MAMC,” J. Mol. Liquids, vol. 158, p. 105, 2011. http://dx.doi.org/10.1016/j.molliq.2010.11.002.

R. M. Melavanki, H. D. Patil, S. Umapathy and J. S. Kadadevaramath, “Solvatochromic Effect on the Photophysical Properties of Two Coumarins,” J. Fluoresc., vol. 22, p. 137, 2012. http://dx.doi.org/ 10.1007/s10895-011-0939-7.

J. J. Aaron, M. D. Gaye, C. Parkanyi, N. S. Cho and L. Von Szentpaly, “Experimental and theoretical dipole moments of purines in their ground and lowest excited singlet states,” J. Mol. Struct., vol. 156,

p. 119, 1987. http://dx.doi.org/10.1016/0022-2860(87)85046-9.

C. Parkanyi, M. R. Stem-Beren, O. R. Martinez, J. J. Aaron, M. B. MacNair and A. F. Arietta, “Solvatochromic correlations and ground- and excited-state dipole moments of curcuminoid dyes,” Spectrochim. Acta Part A. vol. 60, p. 1805, 2004. http://dx.doi.org/ 10.1016/j.saa.2003.07.013.

Kawski, B. Kuklinski and P. Bojarski, “Thermochromic Absorption, Fluorescence Band Shifts and Dipole Moments of BADAN and ACRYLODAN,” Z. Naturforsch, vol. 57A, pp. 716, 2002. http://dx.doi.org/0932-0784 / 02 / 0800-0716.

K. Fukui, T. Yonezawa and H. Shingu, “A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons,” J. Chem. Phys., vol. 20,

p. 722, 1952. http://dx.doi.org/10.1063/1.1700523.

L. Bilot and A. Kawski, “Theorie des Einflusses von Lösungsmitteln auf die Elektronenspektren der Moleküle,” Z. Naturforsch, vol. 17A, p. 621, 1962.

Kawski, “Untersuchungenn zum zwischenmolekularen Energieübergang in Fluoreszierenden Lösungen,” Z. Naturforsch, vol. 18A, p. 961, 1963.

M. J. Frisch, G. W. Trucks and H. B. Schlegel, “Gaussian, Revision B. Gaussian Inc”., Pittsburg, 2003,

K. Gewald, E. Schinke and H. Botcher, “Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen, Carbonylverbindungen und Schwefel,” Chem. Ber. vol. 99, p. 94, 1966. http://dx.doi.org/10.1002/cber.19660990116.

S. Mohan and J. Saravanan, “Synthesis, Characterization and Antibacterial Activity of Some Schiff Bases of 2-Amino-3-(N-Tolyl Carboxamido)-4,5,6,7-Tetrahydro Benzo(b)Thiophenes,” Asian J. Chem. vol. 15, p. 67, 2003. http://www.asianjournalofchemistry.co.in/ User/ViewFreeArticle.aspx?ArticleID=15_1_14.

E. Lippert, “Dipolmoment und elektronstrukturen von angeregten molekülen,” Z. Naturforsch., vol. 10A, p. 541, 1955.

N. G. Bakshiev, “Universal intermolecular interactions and their effect on the position of the electronic spectra of molecules in two component solutions,” Opt. Spectosk. (USSR), vol. 16, p. 821, 1964.

Chamma and P. Viallet, “Determination du moment dipolaire d’une molecule dans un etat excité singulet: application á l’indole, au benzimidazole et á l’indazole,” C. R. Acad. Sci. Paris, Ser., vol. C270, p. 1901, 1970.

M. Ravi, T. Soujanya, A. Samanta and T. P. Radhakrishnan, “Excited-state dipole moments of some Coumarin dyes from a solvatochromic method using the solvent polarity parameter, ENT” J. Chem. Soc. Faraday. Trans., vol. 91, p. 2739, 1995. http://dx.doi.org/ 10.1039/ FT9959102739.

J. T. Edward, “Molecular volumes and Parachor”, Chem, Ind. London, p. 774, 1956.

Published

2013-02-01

Most read articles by the same author(s)