Self-assembly of cyclodextrins with meso-tetrakis(4-sulfonatophenyl)porphyrin in aqueous solution

Ribó, Josep M.; Farrera, Joan‐Anton; Valero, M. Luz; Virgili, Albert

doi:10.1016/0040-4020(95)00085-m

Cited by 75 publications

(37 citation statements)

References 25 publications

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“…The IC formation leaded to the upfield shift of the anomeric hydrogen (H1) of the glucopyranose unit around À0.10 to À0.20 ppm and the downfield shift for the peaks of the secondary hydroxyl groups (O 2 H, O 3 H) about 0.05-0.08 ppm. 36 Neverthe- Figure 1. 1 H-NMR spectra of pure a-CD (A), F-0CD-100 (B), and F-30a-CD-80 (C).…”

Section: Atrp Of Hpma Initiated With Pprs Comprising Brib-f127-ibbr Amentioning

confidence: 99%

Novel main‐chain polyrotaxanes synthesized via ATRP of HPMA in aqueous media

Zhang

Zhu

Tong

et al. 2008

J. Polym. Sci. A Polym. Chem.

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Section: Atrp Of Hpma Initiated With Pprs Comprising Brib-f127-ibbr Amentioning

confidence: 99%

Novel main‐chain polyrotaxanes synthesized via ATRP of HPMA in aqueous media

Zhang

Zhu

Tong

et al. 2008

J. Polym. Sci. A Polym. Chem.

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“…In this sense, the effects on b-CD are different from those on g-CD. This may be attributed to differences in the geometric arrangement of each cyclodextrin detected because of the high magnetic anisotropy of the porphyrin ring [15]. Obviously, the change of chemical shift for the cyclodextrin protons is highest at low cyclodextrin ratios, i.e.…”

Section: Resultsmentioning

confidence: 97%

“…a-CD does not form inclusion complexes with TPPS 4 , because the cyclodextrin cavity is too small for the complexation of the sulfonatophenyl substituent [15,16]. This prevents the structural study of its heteroassociation by 1 H NMR.…”

Section: Introductionmentioning

confidence: 96%

“…This prevents the structural study of its heteroassociation by 1 H NMR. However, TPPS 4 gives soluble inclusion complexes with b-and g-cyclodextrin (b-CD, g-CD) [17][18][19][20][21], the approximate geometry of which has been inferred from 1 H NMR studies [15]. Complexation occurs as expected through the meso-sulfonatophenyl substituents but different geometries have been proposed for the b-CD and the g-CD complexes.…”

Section: Introductionmentioning

confidence: 98%

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Heteroassociation of meso-sulfonatophenylporphyrins with β- and γ-cyclodextrin

Farrera

García-Ortega

Ramirez-Gutierrez

et al. 2001

J. Porphyrins Phthalocyanines

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ABSTRACT:The effect of the addition of b-and g-cyclodextrin (b-CD, g-CD) to water solutions (D 2 O) of the 4'-sulfonato derivatives of meso-tetraphenylporphyrin (TPPS 4 , TPPS 3 , TPPS 2o and TPPS 2a ) was studied by 1 H NMR at several temperatures. In all cases the disaggregation of the porphyrin homoassociates was detected, although in most cases it was only partial. Nuclear Overhauser signals (ROESY) show that cyclodextrin inclusion complexes were formed with TPPS 4 , TPPS 3 , and TPPS 2o , but not with TPPS 2a . These complexes include the sulfonatophenyl groups as guest, but not the hydrophobic phenyl substituents. The geometry of the complexes corresponds to that in which the sulfonatophenyl substituent is introduced through the secondary face of b-CD and through the primary face of g-CD.In the inclusion complexes the polar sulfonato group is inside the cyclodextrin cavity but near to the hydrophilic interface with the bulk water. This explains the absence of complexation in the case of cationic porphyrins such as 5,10,15,20-tetrakis(N-methylpyridin-4-yl)porphyrin (TMPyP), and the decrease in the solubility when the b-CD complex of 5,15-bis(4-sulfonatophenyl)porphyrin (DPPS 2o ) forms. Complexes of the cyclodextrins with porphyrin homoassociates were also detected. This indicates that the heteroassociation avoids the formation of staggered stacks of porphyrin homoassociates, but has less effect on the association through the hydrophobic region of the phenyl substituents. This last type of aggregation, which is not significantly affected by the addition of a-CD, explains why the hydrophobic phenyl substituents are not complexed by the cyclodextrins.

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“…Supromolecular self-assembly is one of the procedures employed for the development of polyfunctional nanoscale receptors. [1][2][3][4][5][6] Thiacalixarene is a readily available macrocyclic platform with great potential for further functionalization. [7][8][9][10][11][12][13][14][15][16] The ability to partial functionalization of the macrocycle [17][18][19] as well as the existence of different spatial isomers make thiacalixarenes essential blocks in the synthesis of selfassembled supramolecular systems, e.g., one-dimensional fibres [20] (supramolecular polymers), two-dimensional sheets [21,22] (vesicles or self-assembled monolayers on surfaces) and three-dimensional solids (metal-organic frameworks).…”

Section: Introductionmentioning

confidence: 99%