Abstract
Three kinds of heteroaldehydes, N-(3-triethoxysilylpropyl)-4-formyl benzamide (TPHA/SiO2), were prepared by the reaction of terephthalaldehydic acid with different silica supports such as hexagonal SBA-15, spherical SBA-15 and amorphous SiO2 for comparison purposes. Anchoring of this aldehyde to different supports allows the synthesis of mono-substituted porphyrins without the production of di-, tri- and tetra-substituted porphyrin side products. The exclusion of the aforementioned side products during the synthesis of monosubstituted porphyrins greatly reduced the complexity during purification of the product. Absorption spectrophotometry was performed on silica gel immobilizing porphyrin (CPTTP), free base tetraphenylporphyrin (H2TPP) and heteroaldehydes (TPHA/SiO2) using UV-Visible instrument and confirmed the presence of porphyrin on the structure of CPTTP.
Similar content being viewed by others
References
Anzenbacher P, Kral V, Jursíkova K, Gunterova J and Kasal A 1997 J. Mol. Catal. A118 63
Adler A D, Longo F R, Finarelli J D, Goldmacher J, Assour J and Korsakoff L 1967 J. Org. Chem. 32 476
Ahmadi E, Nekomanesh Haghighi M, Mohamadnia Z and Ramazani A 2010 J. Appl. Polym. Sci. 118 3658
Choithani J, Kumar P and Gupta K C 2006 Anal. Biochem. 357 240
Fa H B, Zhao L, Wang X Q, Yu J H, Huang Y B, Yang M and Wang D J 2006 Eur. J. Inorg. Chem. 21 4355
Fan H et al 2000 Nature 405 56
Gao B, Wang R and Zhang Y 2009 J. Appl. Polym. Sci. 112 2764
Ghiaci M, Molaie F, Sedaghat M E and Dorostkar N 2010 Catal. Commun. 11 694
Gomez-Romero P and Sanchez C 2004 Functional hybrid materials (Weinheim: Wiley-VCH)
Johanson U, Marandi M, Sammelselg V and Tamm J 2005 J. Electroanal. Chem. 575 267
Kosuge K and Singh P S 2001 Chem. Mater 13 2476
Lindsay Smith J R 2000 The porphyrin handbook (eds) K M Kadish, K M Smith and R Guilard (San Diego: Academic Press) p. 45
Luts T, Suprum W, Hofmann D, Klepel O and Papp H 2007 J. Mol. Catal. A: Chem. 261 16
Latour V, Pigot T, Mocho P, Blanc S and Lacombe S 2005 Catal. Today 101 359
Ma Y, Qi L, Ma J, Wu Y, Liu O and Cheng H 2003 Colloid. Surf. A: Physicochem. Eng. Aspects 229 1
Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoorbaltorkb I and Kargar H 2005 Bioorg. Med. Chem. 13 2901
Mohamadnia Z, Ahmadi E, Nekoomanesh M, Ramazani A and Salehi Mobarakeh H 2010 Polym. Int. 59 945
Naik R, Joshi P, Umbarak S and Deshpande R K 2005 Catal. Commun. 6 125
Pan J H and Lee W I 2005 New J. Chem. 29 841
Qu R, Wang M, Sun C, Zhang Y, Ji C and Chen H 2008 Appl. Surf. Sci. 255 3361
Rahiman A K, Rajesh K, Bharathi K S, Sreedaran S and Narayanan V 2006 Appl. Catal. A: Gen. 314 216
Sacco H C, Ciuffi K J, Biazzotto J C, Zuccki M R, Leite C A P, Nascimento O R and Serra Iamamoto O A 2000 J. Non-Cryst. Solids 273 150
Sacco H C, Iamamoto Y and Lindsay Smith J R 2001 J. Chem. Soc. Perkin Trans. 2 181
Shea K J and Loy D A 2001 Chem. Mater. 13 3306
Steinfeld J I and Wormhoudt J 1998 Annu. Rev. Phys. Chem. 49 203
Santos S F et al 2007 J Colloid Interf. Sci. 305 264
Yang Q, Streb K K and Borhan B 2005 Tetrahedron Lett. 46 6737
Yinon J 2003 Anal. Chem. 75 99
Zheng S, Gao L and Guo J 2000 J. Solid-State Chem. 152 447
Zhang X, Jin Z, Li Y, Li S and Lu G 2007 J. Power Sources 166 74
Zhou Y, Schattka J H and Atonietti M 2004 Nano Lett. 4 477
Zhang L, Sun T and Ying J Y 1999 Chem. Commun. 1103
Zhao D, Sun Q and Stucky G D 2000 Chem. Mater. 12 275
Zhao J W, Gao F, Fu Y L, Jin W, Yang P D and Zhao D Y 2002 Chem. Commun. 752
Zhao D, Huo Q, Feng J, Chmelka B F and Stucky G D 1998 J. Am. Chem. Soc. 120 6024
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Ahmadi, E., Ramazani, A., Mashhadi-Malekzadeh, A. et al. Preparation and characterization of monosubstituted porphyrins immobilized on nanosilica. Bull Mater Sci 37, 1101–1112 (2014). https://doi.org/10.1007/s12034-014-0050-1
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12034-014-0050-1