Effects of meso-substituents and core-modification on photophysical and electrochemical properties of porphyrin–ferrocene conjugates

作者: Smita Rai , G. Gayatri , G. Narahari Sastry , M. Ravikanth

DOI: 10.1016/J.CPLETT.2008.10.076

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摘要: Abstract The effects of meso-substituents and porphyrin core-modification on electronic communication between ferrocene in covalently linked porphyrin–ferrocene conjugates are described. electrochemical photophysical studies indicated that the is strong when five membered aryl groups than six groups. This may be traced to near orthogonal arrangement ring with meso-aryl leading weaker interaction ferrocenyl conjugates, while furyl thienyl closer plane being orthogonal. Molecular orbital performed at semiempirical PM3 BLYP levels rationalize results.

参考文章(19)
Yukiyasu Kashiwagi, Hiroshi Imahori, Yasuyuki Araki, Osamu Ito, Koji Yamada, Yoshiteru Sakata, Shunichi Fukuzumi, Strong Inhibition of Singlet Oxygen Sensitization in Pyridylferrocene−Fluorinated Zinc Porphyrin Supramolecular Complexes Journal of Physical Chemistry A. ,vol. 107, pp. 5515- 5522 ,(2003) , 10.1021/JP034920Q
Xuedong Sun, Jinglong Zhang, Bin He, The synthesis and photochemical characterization of meso-tetra-thienyl porphyrins Journal of Photochemistry and Photobiology A: Chemistry. ,vol. 172, pp. 283- 288 ,(2005) , 10.1016/J.JPHOTOCHEM.2004.12.016
Daniel T. Gryko, Feng Zhao, Amir A. Yasseri, Kristian M. Roth, David F. Bocian, Werner G. Kuhr, Jonathan S. Lindsey, Synthesis of thiol-derivatized ferrocene-porphyrins for studies of multibit information storage Journal of Organic Chemistry. ,vol. 65, pp. 7356- 7362 ,(2000) , 10.1021/JO0004862
Won-Seob Cho, Han-Je Kim, Benjamin J. Littler, Mark A. Miller, Chang-Hee Lee, Jonathan S. Lindsey, Rational Synthesis of Trans-Substituted Porphyrin Building Blocks Containing One Sulfur or Oxygen Atom in Place of Nitrogen at a Designated Site Journal of Organic Chemistry. ,vol. 64, pp. 7890- 7901 ,(1999) , 10.1021/JO9909305
Iti Gupta, M. Ravikanth, Recent developments in heteroporphyrins and their analogues Coordination Chemistry Reviews. ,vol. 250, pp. 468- 518 ,(2006) , 10.1016/J.CCR.2005.10.010
Jonathan Rochford, A. Denise Rooney, Mary T. Pryce, Redox control of meso-zinc(II) ferrocenylporphyrin based fluorescence switches. Inorganic Chemistry. ,vol. 46, pp. 7247- 7249 ,(2007) , 10.1021/IC0703326
Lechoslaw Latos-Grazynski, Jerzy Lisowski, Marilyn M. Olmstead, Alan L. Balch, 21-Thiatetra-p-tolylporphyrin and its copper(II) bicarbonate complex: structural effects of copper-thiophene binding Journal of the American Chemical Society. ,vol. 109, pp. 4428- 4429 ,(1987) , 10.1021/JA00248A067
Richard W. Wagner, Thomas E. Johnson, Feirong Li, Jonathan S. Lindsey, Synthesis of Ethyne-Linked or Butadiyne-Linked Porphyrin Arrays Using Mild, Copper-Free, Pd-Mediated Coupling Reactions Journal of Organic Chemistry. ,vol. 60, pp. 5266- 5273 ,(1995) , 10.1021/JO00121A052
Jonathan S. Lindsey, Irwin C. Schreiman, Henry C. Hsu, Patrick C. Kearney, Anne M. Marguerettaz, Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions Journal of Organic Chemistry. ,vol. 52, pp. 827- 836 ,(1987) , 10.1021/JO00381A022