2019
DOI: 10.1002/cctc.201900968
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Copper‐Coordinated Histidyl Bolaamphiphile Assembly as an Oxidative Catalyst: Coordination Structure and Catalytic Activity in Cyclohexane Oxidation

Abstract: Surface‐exposed imidazole moieties of a supramolecular self‐assembly of histidyl bolaamphiphile (HisC7) readily coordinate at transition metal ions. In this study, the Cu‐coordinated histidyl bolaamphiphile assembly (HisC7[Cu]) is demonstrated to be an effective oxidative catalyst, with a Fenton‐active copper center. HisC7[Cu] catalytically oxidized cyclohexane to produce cyclohexanol in the yield of 20.2 %, which is comparable to other homogeneous catalysts. The coordination sphere of the active copper center… Show more

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Cited by 9 publications
(14 citation statements)
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“…Lee and co-workers coordinated Cu 2+ to self-assembled histidyl bolaamphiphiles to produce Fenton-active copper centers. 164 In the presence of H 2 O 2 , the supramolecular catalyst catalyzed the oxidization of cyclohexane to produce cyclohexanol. The yield was as high as 20.2%, when the catalyst was prepared at HisC7/ Cu molar ratio of 0.75, corresponding to a N1O3 coordination sphere of copper center.…”
Section: Design Fabrication and Applications Of Enzyme-mimicking Supr...mentioning
confidence: 99%
See 1 more Smart Citation
“…Lee and co-workers coordinated Cu 2+ to self-assembled histidyl bolaamphiphiles to produce Fenton-active copper centers. 164 In the presence of H 2 O 2 , the supramolecular catalyst catalyzed the oxidization of cyclohexane to produce cyclohexanol. The yield was as high as 20.2%, when the catalyst was prepared at HisC7/ Cu molar ratio of 0.75, corresponding to a N1O3 coordination sphere of copper center.…”
Section: Design Fabrication and Applications Of Enzyme-mimicking Supr...mentioning
confidence: 99%
“…Moreover, the enantioselectivity (i.e., configuration of the products) could be reversed by the use of the opposite enantiomer of the amphiphilic compound, which indicated the formation of the chiral catalytic site from the assembling blocks. Lee and co-workers coordinated Cu 2+ to self-assembled histidyl bolaamphiphiles to produce Fenton-active copper centers . In the presence of H 2 O 2 , the supramolecular catalyst catalyzed the oxidization of cyclohexane to produce cyclohexanol.…”
Section: Design Fabrication and Applications Of Enzyme-mimicking Supr...mentioning
confidence: 99%
“…S18 (ESI †), the intensities of characteristic absorption peaks at 1533-1539 cm À1 , corresponding to the imidazole N-H bending vibration, were attenuated and shifted to 1541 cm À1 , once peptides were mixed with Cu 2+ ions. 40,41 Simultaneously, absorption peaks at 3271-3287 cm À1 and 1589-1601 cm À1 attributed to the N-H stretching vibration and N-H bending vibration of amide groups decreased dramatically upon the addition of Cu 2+ ions. [42][43][44] However, the absorption band at 939-945 cm À1 which was ascribed to the outof-plane bending vibration absorption of the carboxylic acid -OH group disappeared after the addition of Cu 2+ ions.…”
Section: Resultsmentioning
confidence: 92%
“…This peroxidase analogue was applied to aniline polymerization and metabolite detection. Considerable catalytic activity for water oxidation was also displayed from the Ir-coordinated bola 7 assembly whose turnover frequency is comparable to other organometallic homogeneous catalysts . In addition, the Cu-coordinated bola 7 showed oxidative catalytic activity allowing for cyclohexane oxidation . These examples imply that the peptidic bola assembly is beneficial for the preparation of metalloenzyme-mimetic catalyst where the peptide motifs act as coordinating ligands to various transition metal ions.…”
Section: Applications Of the Self-assembled Peptidic And Amino Acid B...mentioning
confidence: 93%
“…116 In addition, the Cu-coordinated bola 7 showed oxidative catalytic activity allowing for cyclohexane oxidation. 117 These examples imply that the peptidic bola assembly is beneficial for the preparation of metalloenzyme-mimetic catalyst where the peptide motifs act as coordinating ligands to various transition metal ions.…”
Section: Applications Of the Self-assembledmentioning
confidence: 99%