European Journal of Chemistry

The investigation of the photophysical properties of α-chlorocurcumin and α-methylcurcumin



Main Article Content

Bahjat Ali Saeed

Abstract

The electronic properties of α-chlorocurcumin and α-methylcurcumin was theoretically investigated at the B3LYP/6-311++G(d,p) level of theory. The thermodynamics quantities were estimated by calculating the frequencies of the molecules. Three main isomers were predicted after full geometry optimization of various suggested isomers within the tautomeric mixture of each molecule; the cis-enol, trans-enol and the trans-diketo isomers. Their stability was in the sequence: cis-enol > trans-diketo > trans-enol. The stabilization energy for the cis-enol with respect to trans-diketo and trans-enol in chlorocurcumin is 8.44 and 12.59 kcal/mol, respectively, while in methylcurcumin, it is 4.80 and 10.79 kcal/mol, respectively. The fluorescence spectra were recorded for the investigated compounds in several protic and aprotic solvent with different dielectric constants and H-bonding abilities. The emission maxima are within the range 487 to 571 nm in ethylene glycol, while they are within the range 475 to 557 nm in n-hexane. The fluorescence quantum yields of both compounds are low and lower than those of curcumin. The quantum yield of chlorocurcumin ranges from ΦFl = 0.008 in MeOH to ΦFl = 0.058 in toluene, while for methylcurcumin it ranges from ΦFl = 0.007 in DMF to ΦFl = 0.0524 in ethylene glycol. The fluorescence of both compounds quenched by water and their fluorescence life times are estimated from the slopes of the linear curves that obtained from Stern-Volmer relationship to be 1.44 and 1.40 psec for chlorocurcumin and methylcurcumin, respectively.


icon graph This Abstract was viewed 1465 times | icon graph Article PDF downloaded 793 times

How to Cite
(1)
Saeed, B. A. The Investigation of the Photophysical Properties of α-Chlorocurcumin and α-Methylcurcumin. Eur. J. Chem. 2015, 6, 279-286.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Liu, K.; Guo, T. L.; Lee, H. G.; Chojnacki, J.; Lee, H. G.; Wang, X.; Siedlak, S. I.; Rao, W.; Zhu, X.; Zhang, Sh. ACS Chem. Neurosci 2012, 3, 141-146.
http://dx.doi.org/10.1021/cn200122j

[2]. Chen, Z. G.; Zhu, L.; Chen, J. H.; Guo, Z. M. Spectrochim. Acta A 2009, 72, 518-522.
http://dx.doi.org/10.1016/j.saa.2008.10.034

[3]. Esatbeyouglu, T.; Huebbe, P.; Emst, I. M. A.; Chin, D.; Wanger, A. E.; Rimbach, G. Angew. Chem. Int. Ed. 2012, 51, 5308-5332.
http://dx.doi.org/10.1002/anie.201107724

[4]. Dahl, T. A.; McGowan, W. M.; Shand, M. A.; Srinivasan, V. S. Arch. Microbiol. 1989, 151, 183-185.
http://dx.doi.org/10.1007/BF00414437

[5]. Haukvik, T.; Bruzell, E.; Kristensen, S.; Tonnesen, H. H. Pharmazie 2010, 65, 600-606.

[6]. Haukvik, T.; Bruzell, E.; Kristensen, S.; Tonnesen, H. H. Pharmazie 2011, 66, 69-74.

[7]. Dahl, T. A.; Bilski, P.; Reszka, K. J.; Chignell, C. F. Photochem. Photobiol. 1994, 59, 290-294.
http://dx.doi.org/10.1111/j.1751-1097.1994.tb05036.x

[8]. Hegge, A. B.; Nielsen, T. T.; Larsen, K. L.; Bruzell, E.; Tonnesen, H. H. Photochem. Photobiol. 2012, 101, 1524-1537.

[9]. Gilli, G.; Bertolasi, V. In: Rappoport, Z. (Ed.) The chemistry of enols. Wiley, New York, 1990.

[10]. Patra, D.; Malaeb, N. N. Luminescence 2012, 27, 11-15.
http://dx.doi.org/10.1002/bio.1313

[11]. Tonnesen, H. H.; Vries, H.; Karlsen, J.; Vanhenegouwen, J. B. J. Pharm. Sci. 1987, 76, 371-373.
http://dx.doi.org/10.1002/jps.2600760506

[12]. Gorman, A. A.; Hamblett, I.; Srinivasan, V. S.; Wood, P. D. Photochem. Photobiol. 1994, 59, 389-398.
http://dx.doi.org/10.1111/j.1751-1097.1994.tb05053.x

[13]. Chan, W. H.; Wu, H. J. J. Cell. Biochem. 2004, 92, 200-212.
http://dx.doi.org/10.1002/jcb.20059

[14]. Koon, H.; Leung, A. W. N.; Yue, K. K. M.; Mak, N. K. J. Environ. Pathol. Toxicol. Oncol. 2006, 25, 205-216.
http://dx.doi.org/10.1615/JEnvironPatholToxicolOncol.v25.i1-2.120

[15]. Park, K.; Lee, J. H. Oncol. Rep. 2007, 17, 537-540.

[16]. Lao, C. D.; Demierre, M. F.; Sondok, V. K. Exp. Rev. Anticancer Ther. 2006, 6, 1559-1568.
http://dx.doi.org/10.1586/14737140.6.11.1559

[17]. Odot, J.; Albert, P.; Carlier, A.; Tarpin, M.; Devy, J.; Madoulet, C. Int. J. Cancer 2004, 111, 381-387.
http://dx.doi.org/10.1002/ijc.20160

[18]. Siwak, D. R.; Shishodia, S.; Aggarwal, B. B.; Kurzrock, R. Cancer 2005, 104, 879-890.
http://dx.doi.org/10.1002/cncr.21216

[19]. Khopde, S. M.; Priyadarsini, K. I.; Palit, D. K.; Mukherjee, T. Photochem. Photobiol. 2000, 72, 625-631.
http://dx.doi.org/10.1562/0031-8655(2000)072<0625:EOSOTE>2.0.CO;2

[20]. Chignell, C. F.; Bilskj, P.; Reszka, K. J.; Motten, A. G.; Sik, R. H.; Dahl, T. A. Photochem. Photobiol. 1994, 59, 295-302.
http://dx.doi.org/10.1111/j.1751-1097.1994.tb05037.x

[21]. Iwunze, M. O. Monats. Chem. 2004, 135, 231-240.
http://dx.doi.org/10.1007/s00706-003-0112-3

[22]. Nardo, L.; Paderno, R.; Andreoni, A.; Masson, M.; Haukvik, T.; Tonnesen, H. H. Spectroscopy 2008, 22, 187-198.
http://dx.doi.org/10.1155/2008/928407

[23]. Kee, T. W.; Adhikary, P.; Carlson, P. J.; Mukherjee, P.; Petrich, J. W. Aust. J. Chem. 2011, 64, 23-30.
http://dx.doi.org/10.1071/CH10417

[24]. Khodpe, S. M.; Priyadarsini, K. I.; Venkatesan, P.; Rao, M. N. A. Biophys. Chem. 1999, 80, 85-91.
http://dx.doi.org/10.1016/S0301-4622(99)00070-8

[25]. Priyadarsini, K. I. Free Radic. Biol. Med. 1997, 23, 838-845.
http://dx.doi.org/10.1016/S0891-5849(97)00026-9

[26]. Patra, D.; Malaeb, N. N. Luminescence 2012, 27, 11-15.
http://dx.doi.org/10.1002/bio.1313

[27]. Khumsupan, P.; Ramires, R.; Khumsupan, D.; Narayanaswami, V. Biochim. Biophys. Acta 2011, 1808, 352-359.

[28]. Priyadarsini, K. I. J. Photochem. Photobiol. C: Photochem. Rev. 2009, 10, 81-95.
http://dx.doi.org/10.1016/j.jphotochemrev.2009.05.001

[29]. Sahu, A.; Kasoju, N.; Bora, U. Biomicromolecules 2008, 9, 2905-2912.
http://dx.doi.org/10.1021/bm800683f

[30]. Wang, F.; Yang, J.; Wu, X.; Wang, F.; Liu, Sh. Anal. Bioanal. Chem. 2006, 385, 139-145.
http://dx.doi.org/10.1007/s00216-006-0372-y

[31]. Baglole, K. N.; Boland, P. G.; Wagner, B. D. J. Photochem. Photobiol. A: Chem. 2005, 173, 230-237.
http://dx.doi.org/10.1016/j.jphotochem.2005.04.002

[32]. Rankin, M. A.; Wagner, B. D. Supramol. Chem. 2004, 16, 513-519.
http://dx.doi.org/10.1080/10610270412331283583

[33]. Xu, G.; Wa, D.; Wang, J.; Jiang, B.; Wang, M.; Xue, X.; Zhou, S.; Wu, B.; Jiang, M. Dyes Pigm. 2014, 101, 312-317.
http://dx.doi.org/10.1016/j.dyepig.2013.09.034

[34]. Seltzer, M. D.; Fallis, S.; Hollins, R. A; Prokopuk, N.; Bui, R. N. J. Flouresc. 2005, 15, 597-603.
http://dx.doi.org/10.1007/s10895-005-2832-8

[35]. Nardo, L.; Andreoni, A.; Bondani, M.; Masson, M.; Tonnesen, H. H. J. Photochem. Photobiol. B: Biology 2009, 97, 77-88.
http://dx.doi.org/10.1016/j.jphotobiol.2009.08.004

[36]. Caselli, M.; Ferrari, E.; Imbriano, C.; Pignedoli, F. J. Photochem. Photobiol. A: Chem. 2010, 210, 115-124.
http://dx.doi.org/10.1016/j.jphotochem.2010.01.008

[37]. Nardo, L.; Andreoni, A.; Masson, M.; Haukvik, T.; Tonnesen, H. H. J. Fluoresc. 2011, 21, 627-635.
http://dx.doi.org/10.1007/s10895-010-0750-x

[38]. Nardo, L.; Andreoni, A.; Bodani, M.; Masson, M.; Haukvik, T.; Tonnesen, H. H. J. Fluoresc. 2012, 22, 597-608.
http://dx.doi.org/10.1007/s10895-011-0995-z

[39]. Bong, P. H. Bull. Korean Chem. Soc. 2000, 2, 81-86.

[40]. Menelaou, M.; Ouharrou, F.; Rodriguez, L.; Roubeau, O.; Teat, S. J.; Aliaga-Alcalde, N. Chem. Eur. J. 2012, 18, 11545-11549.
http://dx.doi.org/10.1002/chem.201200955

[41]. Wang, F.; Huang, W.; Wang, Y. J. Luminescence 2008, 128, 110-116.
http://dx.doi.org/10.1016/j.jlumin.2007.05.012

[42]. Al-Salim, T., Ph.D. Thesis, University of Basrah, 2013.

[43]. Velapoldi, R.; Tonnesen, H. H. J. Fluoresc. 2004, 14, 465-472.
http://dx.doi.org/10.1023/B:JOFL.0000031828.96368.c1

[44]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D. 01, Gaussian, Inc., Wallingford CT, 2009.

[45]. Parr, R. G.; Wang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press, New York, 1989.

[46]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
http://dx.doi.org/10.1063/1.464913

[47]. Runge, E.; Gross, E. K. U. Phys. Rev. Lett. 1984, 52, 997-1000.
http://dx.doi.org/10.1103/PhysRevLett.52.997

[48]. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110-114116.
http://dx.doi.org/10.1063/1.3359469

[49]. Balasubramanian, K. J. Agric. Food. Chem. 2006, 54, 3512-3520.
http://dx.doi.org/10.1021/jf0603533

[50]. Shen. L.; Ji, H. F. Spectrochim. Acta A 2007, 67, 619-623.
http://dx.doi.org/10.1016/j.saa.2006.08.018

[51]. Bassetti, M.; Gerichelli, G.; Floris, B. Tetrahedron 1988, 44, 2997-3004.

[52]. Manbeck, K. A.; Boaz, N. C.; Bair, N. C., Sanders, A. M. S.; Marsh, A. L. J. Chem. Educ. 2011, 88, 1444-1445.
http://dx.doi.org/10.1021/ed1010932

[53]. Zsila, F.; Bikadi, Z.; Simony, M. Tetrahedron: Asymm. 2003, 14, 2433-2444.
http://dx.doi.org/10.1016/S0957-4166(03)00486-5

[54]. Belova, N. V.; Oberhammer, H.; Girichev, G. V.; Shylkov, A. J. Phys. Chem. A 2008, 112, 3209-3214.
http://dx.doi.org/10.1021/jp711290e

[55]. Moriya, T. Bull. Chem. Soc. Jpn. 1984, 57, 1723-1730.
http://dx.doi.org/10.1246/bcsj.57.1723

Supporting Agencies

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).