Mn-tetraarylporphyrins bearing N-alkyl sulphonamido tails: effect of the length and polarity of the chains on physical properties and reactivity

Banfi, Stefano; Cavalieri, Claudio; Cavazzini, Marco; Trebicka, Artan

doi:10.1016/s1381-1169(99)00239-3

Cited by 9 publications

(5 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…23,[25][26][27][28][29][30] Thus, adding an excess of the desired amine to a dichloromethane solution of the chlorosulfonated porphyrin derivatives 4, 5 and 6, and maintaining the reaction at room temperature for 3 h, yields the corresponding sulfonamides (4a-e; 5a-e; 6a-e, see Scheme 1). After work-up, we isolated our portfolio of amphiphilic sulfonamide porphyrin derivatives with yields up to 75% (see Table 1).…”

Section: Sulfonamide Synthesismentioning

confidence: 99%

“…12,25,26 These chlorosulfonates revealed also excellent reactivities towards nucleophiles like water, amines, alcohols or amino acids. 12,[23][24][25][26][27][28] Metallocomplexes of amphiphilic sulfonamide porphyrins proved to be quite good catalysts for epoxidation of alkenes 29 and oxidation of azo dyes in biphasic systems using hydrogen peroxide as oxidant. 30 Furthermore, the synthesis of amphiphilic corroles with sulfonic acid head groups and their multiple applications on bio-mimetic catalysis, 31,32 bio-medicine 33,34 and photovoltaic cells 35 have been recently described by Gross.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

et al. 2008

View full text Add to dashboard Cite

a b s t r a c tPorphyrins are key precursors for development of photosensitizers for photodynamic therapy. A new series of ortho-halogenated tetraarylporphyrins with sulfonamide substituents have been synthesized via chlorosulfonation reaction and characterized by MALDI-TOFMS. To predict their partition properties, log K OW of a selected range of the synthesized halogenated amphiphilic porphyrins is described. A significant effect of the number and type of halogen group as well as on the number of sulfonamide side chain was observed. The determined 1-octanol/water partition coefficients showed that it is possible to obtain compounds with a wide range of lipophilicities, from log K OW ¼À2.71 till log K OW >4, which are suitable to optimize the biological efficacy of this class of sensitizers.

show abstract

Section: Sulfonamide Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

et al. 2008

View full text Add to dashboard Cite

show abstract

“…The first level is the design of the homogeneous epoxidation catalyst. Catalyst performance can be optimized by modification of the ligand and the central transition metal atom (8)(9)(10). At the second level, the micelle-catalyst combination is designed for optimal contacting of catalyst and reactants on a molecular scale.…”

Section: Introductionmentioning

confidence: 99%

Micellar Catalysis as a Clean Alternative for Selective Epoxidation Reactions

Heijnen

Bruijn

Broeke

et al. 2002

ACS Symposium Series

View full text Add to dashboard Cite

In the search for more environmentally friendly processes, the use of micellar structures opens up a range of new possibilities. One of the most exciting applications is the incorporation of homogeneous catalysts in micelles to perform reactions: micellar catalysis. Micellar catalysis can be used to perform for example epoxidation reactions. In this way organic solvents, in which epoxidations are usually performed, are replaced by aqueous surfactant solutions. In this study propylene and 1-octene have been successfully epoxidized by hydrogen peroxide, catalyzed by micelle -incorporated porphyrin catalysts. Furthermore, several experimental techniques have been used to get more insight in the micelle-catalyst system.

show abstract

“…For epoxidation reactions, a number of catalysts are available. Porphyrins have been used for selective epoxidation of propene and other terminal alkenes using micellar systems, but in most cases an organic medium has been used. − An advantage of porphyrin catalysts is the ability to tune the reactivity, selectivity, and stability by modifications of the porphyrin macrocycle. , Other catalysts used for epoxidation reactions are salen complexes , and methyltrioxorhenium-based catalysts. , For the epoxidation of propene, also heterogeneous zeolite systems and immobilized catalytic systems , have been used.…”

Section: Introductionmentioning

confidence: 99%

“…[6][7][8] An advantage of porphyrin catalysts is the ability to tune the reactivity, selectivity, and stability by modifications of the porphyrin macrocycle. 9,10 Other catalysts used for epoxidation reactions are salen complexes 11,12 and methyltrioxorhenium-based catalysts. 13,14 For the epoxidation of propene, also heterogeneous zeolite systems 15 and immobilized catalytic systems 16,17 have been used.…”

Section: Introductionmentioning

confidence: 99%

Micellar Catalysis for Epoxidation Reactions

Broeke

Bruijn

Heijnen

et al. 2001

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

The epoxidation of 1-octene and propene with hydrogen peroxide is performed using micellar catalysis. Linear terminal alkenes have successfully been epoxidized with a homogeneous catalyst solubilized in an aqueous micellar solution. The best micellar system, in terms of reactivity and activity, consists of a homogeneous porphyrin catalyst, Mn(TDCPP)Cl, solubilized in Triton X-100 micelles. The aggregation behavior of Triton X-100 micelles with and without different epoxidation catalysts has been studied. For the epoxidation of 1-octene with the Mn(TDCPP)-Cl-Triton X-100 system, a conversion of about 25% with a selectivity toward octene oxide in excess of 97% was obtained after 30 min. The cocatalyst used was imidazole. The initial turnover frequency was 250 h -1 . The Mn(TDCPP)Cl-Triton X-100 system showed excellent stability, and virtually no deactivation of the porphyrin catalyst was observed. The same epoxidation reaction carried out in a mixture of dichloromethane and CH 3 CN had an initial turnover frequency of 392 h -1 , and the selectivity toward octene oxide was 94%.

show abstract

Mn-tetraarylporphyrins bearing N-alkyl sulphonamido tails: effect of the length and polarity of the chains on physical properties and reactivity

Cited by 9 publications

References 25 publications

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

Micellar Catalysis as a Clean Alternative for Selective Epoxidation Reactions

Micellar Catalysis for Epoxidation Reactions

Contact Info

Product

Resources

About