Protonated sapphyrins. Highly effective phosphate receptors

Journal of the American Chemical Society

Volumn 118, Issue 7, 1996, Pages 1595-1607

  Král, Vladimír ^a   Furuta, Hiroyuki ^a   Shreder, Kevin ^a   Lynch, Vincent ^a   Sessler, Jonathan L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE PHOSPHATE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PORPHYRIN DERIVATIVE; SAPPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; COMPLEX FORMATION; DRUG RECEPTOR BINDING; MASS SPECTROMETRY; MODEL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030002361     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9529605     Document Type: Article

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103. 17b visible spectroscopy provides a very convenient means of assessing sapphyrin-sapphvrin aggregation: The characteristic Soret-type absorbance band of sapphyrin (free-base, mono- or diprotonated) appears at 445-450 nm when it is monomeric. at ca. 420 nm when it is dimeric. and at ca. 400 nm when it is more highly aggregated.
104. - types difficult (corresponding to the equilibria of eqs 3 and 5, respectively) by this means
105. 4
106. The magnitude of the shifts was always greater in the case of phenylphosphonate than in the case of the dihydrogen phosphate which we interpret in terms of better binding interactions with phenylphosphonate. These we suggest could result from an extra stabilization arising from favorable π-π stacking effects present in the case of the phenylphosphonate complex and would be analogous to those seen in the solid-state structure of the 2 1 phenyl phosphate-sapphyrin complex shown in Figure 4.
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109. 4 that are displaced upfield by only 3.23 and 2.93 ppm. respectively, relative to those of the free-acid form.
110. Many other titrations were also carried out using a range of other phosphate-sapphyrin mixtures with both compounds being m sarious protonation states, e.g., free-base, mono- and diprotonated sapphyrin. free-acid, mono- and dibasic phosphate acids. See Supporting Information
111. In these experiments, the sapphyrin methine protons could also be monitored. As expected, these sets of signals also moved to higher field as complexation was allowed to occur.
112. a determinations. A nonionic detergent was employed in this study to avoid difficulties involving the precipitation of the neutral macrocycle at high pH. Interestingly, the monocation of sapphyrin 1 is clearly stable under these conditions, a phenomenon that, to the best of our know ledge, has not been observable with octaalkyl porphyrins in the presence of nonionic detergents. See. Phillips, J. N. In Current Trends in Heterocyclic Chemistry: Alberts, A., Badger, G. M., Shoppee, C. W., Eds : Academic Press. Inc New York, 1958. pp 30-39