1985
DOI: 10.1139/v85-099
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Preparation and properties of a linked porphyrin–cyclodextrin

Abstract: . Can. J . Chem. 63, 602 (1985).The synthesis of the linked porphyrin-cyclodextrin 3 and its zinc complex 4 is described and their characterization by ' H nmr, ''C nmr, circular dichroism, ultraviolet, and infrared spectroscopy is reported. The linked porphyrin-cyclodextrin compounds exhibited perturbed electronic absorption and emission spectra which are consistent with their adopting two conformations, one extended with little interaction between the porphyrin and cyclodextrin, and the other folded with the … Show more

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Cited by 28 publications
(6 citation statements)
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“…Initial studies on phenyl-substituted porphyrin-CD inclusion complexes were inspired by mimicking photosynthetic reaction centers [ 170 ] or protein containing porphyrins such as hemoglobin, myoglobin or cytochromes where the CD cavity mimics the protein hydrophobic pockets to obtain water-soluble artificial analogues for mechanistic investigations [ 171 , 172 , 173 , 174 ]. Numerous studies have addressed the CD inclusion of meso -tetrakis (4-sulfonatophenyl) porphyrin (TPPS 4 ) and its metal complexes that exhibit aggregation in aqueous solutions [ 175 , 176 ].…”
Section: Applications To Study Porphyrin–macromolecule Interactionmentioning
confidence: 99%
“…Initial studies on phenyl-substituted porphyrin-CD inclusion complexes were inspired by mimicking photosynthetic reaction centers [ 170 ] or protein containing porphyrins such as hemoglobin, myoglobin or cytochromes where the CD cavity mimics the protein hydrophobic pockets to obtain water-soluble artificial analogues for mechanistic investigations [ 171 , 172 , 173 , 174 ]. Numerous studies have addressed the CD inclusion of meso -tetrakis (4-sulfonatophenyl) porphyrin (TPPS 4 ) and its metal complexes that exhibit aggregation in aqueous solutions [ 175 , 176 ].…”
Section: Applications To Study Porphyrin–macromolecule Interactionmentioning
confidence: 99%
“…Furthermore, nitro and amino groups can be easily functionalized, 11,13,14 and conjugated with bioactive molecules, such as monoclonal antibodies, 15 oligomeric carboranyl phosphate diesters, 16 polymer backbones, 17 and cyclodextrins. 18 Current synthetic routes to mono-, di-and tri-nitro functionalized meso-tetraphenylporphyrins involve total synthesis via a crossed Rothemund approach, 17 or by electrophilic nitration of the p-phenyl groups of mesotetraphenylporphyrin (TPP, 1). 19,20 In the first method co-condensation of pyrrole, benzaldehyde and nitrobenzaldehyde, results in low to moderate yields of the targeted porphyrins, which can be tedious to purify from the resulting reaction mixtures.…”
Section: Introductionmentioning
confidence: 99%
“…[1][2][3][4][5][6][7][8][9][10][11][12]19,21] The several porphyrin derivatives covalently linked with cyclodextrins were synthesized and investigated. [2][3][4][6][7][8][9][10][11][12]20,[22][23][24][25][26][27][28][29][30][31][32][33][34] Most of these conjugates contain one or two cyclodextrin units on periphery of porphyrin macrocycle. In general, as evidenced from experimental data, the cyclodextrin containing porphyrins with one and two cyclodextrin fragments are formed supramolecular complexes due to deep inclusion of unsubstituted phenyl groups in the CD cavity.…”
Section: Introductionmentioning
confidence: 99%