N-Derivatives of peri-Substituted Dichalcogenide[FeFe]-Hydrogenase Mimics: Towards Photocatalytic Dyads for Hydrogen Production

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N-Derivatives of peri-Substituted Dichalcogenide[FeFe]-Hydrogenase Mimics: Towards Photocatalytic Dyads for Hydrogen Production. / Figliola, Carlotta; Male, Louise; Horswell, Sarah L; Grainger, Richard S.

In: European Journal of Inorganic Chemistry, Vol. 2015, No. 19, 07.07.2015, p. 3146-56.

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@article{8a1a57db132042178d19f8f7d81bbf7e,
title = "N-Derivatives of peri-Substituted Dichalcogenide[FeFe]-Hydrogenase Mimics: Towards Photocatalytic Dyads for Hydrogen Production",
abstract = "Synthetic strategies towards molecular dyads based on peri-substituted dichalcogenide (S,Se) [FeFe]-hydrogenase synthetic mimics covalently linked to a ZnTPP photosensitizer are described. Dithiolate and diselenolate model systems 2–5 are prepared through condensation of 2-naphthaldehydes with p-methoxyaniline, reduction of the resulting Schiff base and oxidative insertion of Fe2(CO)6 into the dichalcogen bond of the imine or amine. Diselenolate-based [FeFe] complexes (imine 3 and amine 5) are more efficient in electrocatalysis of proton reduction than their sulfur analogues 2 and 4 with increasing concentrations of pTsOH. Molecular dyad 1 containing a peri-substituted naphthalene dithiolate Fe2(CO)6 cluster covalently linked via an amine to ZnTPP is prepared through sequential zinc insertion into the porphyrin followed by iron insertion into the disulfide bond",
keywords = "Photocatalysis, Electrocatalysis, Cyclic voltammetry, Porphyrinoids, Carbonyl ligands",
author = "Carlotta Figliola and Louise Male and Horswell, {Sarah L} and Grainger, {Richard S}",
year = "2015",
month = jul,
day = "7",
doi = "10.1002/ejic.201500355",
language = "English",
volume = "2015",
pages = "3146--56",
journal = "European Journal of Inorganic Chemistry",
issn = "1434-1948",
publisher = "Wiley-VCH Verlag",
number = "19",

}

RIS

TY - JOUR

T1 - N-Derivatives of peri-Substituted Dichalcogenide[FeFe]-Hydrogenase Mimics: Towards Photocatalytic Dyads for Hydrogen Production

AU - Figliola, Carlotta

AU - Male, Louise

AU - Horswell, Sarah L

AU - Grainger, Richard S

PY - 2015/7/7

Y1 - 2015/7/7

N2 - Synthetic strategies towards molecular dyads based on peri-substituted dichalcogenide (S,Se) [FeFe]-hydrogenase synthetic mimics covalently linked to a ZnTPP photosensitizer are described. Dithiolate and diselenolate model systems 2–5 are prepared through condensation of 2-naphthaldehydes with p-methoxyaniline, reduction of the resulting Schiff base and oxidative insertion of Fe2(CO)6 into the dichalcogen bond of the imine or amine. Diselenolate-based [FeFe] complexes (imine 3 and amine 5) are more efficient in electrocatalysis of proton reduction than their sulfur analogues 2 and 4 with increasing concentrations of pTsOH. Molecular dyad 1 containing a peri-substituted naphthalene dithiolate Fe2(CO)6 cluster covalently linked via an amine to ZnTPP is prepared through sequential zinc insertion into the porphyrin followed by iron insertion into the disulfide bond

AB - Synthetic strategies towards molecular dyads based on peri-substituted dichalcogenide (S,Se) [FeFe]-hydrogenase synthetic mimics covalently linked to a ZnTPP photosensitizer are described. Dithiolate and diselenolate model systems 2–5 are prepared through condensation of 2-naphthaldehydes with p-methoxyaniline, reduction of the resulting Schiff base and oxidative insertion of Fe2(CO)6 into the dichalcogen bond of the imine or amine. Diselenolate-based [FeFe] complexes (imine 3 and amine 5) are more efficient in electrocatalysis of proton reduction than their sulfur analogues 2 and 4 with increasing concentrations of pTsOH. Molecular dyad 1 containing a peri-substituted naphthalene dithiolate Fe2(CO)6 cluster covalently linked via an amine to ZnTPP is prepared through sequential zinc insertion into the porphyrin followed by iron insertion into the disulfide bond

KW - Photocatalysis

KW - Electrocatalysis

KW - Cyclic voltammetry

KW - Porphyrinoids

KW - Carbonyl ligands

U2 - 10.1002/ejic.201500355

DO - 10.1002/ejic.201500355

M3 - Article

VL - 2015

SP - 3146

EP - 3156

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

SN - 1434-1948

IS - 19

ER -