ChemInform Abstract: Electronic Communication in Tetrathiafulvalene (TTF)/C<sub>60</sub> Systems: Toward Molecular Solar Energy Conversion Materials?

Martı́n, Nazario; Sánchez, Luis; Herranz, M. Ángeles; Illescas, Beatriz M.; Guldi, Dirk M.

doi:10.1002/chin.200802279

Cited by 3 publications

(6 citation statements)

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“…copper complex catalyst | donor-acceptor dyad | nanosized silica-alumina | p-xylene | photoinduced electron transfer E xtensive efforts have been devoted to develop a variety of electron donor-acceptor linked molecules, which mimic charge-separation processes in the photosynthetic reaction center (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11); however, long-lived charge separation has been attained only in frozen media at low temperature (12)(13)(14)(15)(16)(17)(18) because intermolecular back electron transfer in solution is predominant as compared to the corresponding intramolecular process. For example, photoexcitation of a charge-shift type donor-acceptor dyad, 9-mesityl-10-methylacridinium ion (Acr þ -Mes) affords the electron-transfer (ET) state (Acr • -Mes •þ ) with an extremely long lifetime (e.g., 2 h at 203 K) in frozen media (18,19).…”

mentioning

confidence: 99%

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Fukuzumi

Doi

Itoh

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

119

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A simple donor-acceptor linked dyad, 9-mesityl-10-methylacridinium ion (Acr þ -Mes) was incorporated into nanosized mesoporous silica-alumina to form a composite, which in acetonitrile is highly dispersed. In this medium, upon visible light irradiation, the formation of an extremely long-lived electron-transfer state (Acr • -Mes •þ ) was confirmed by EPR and laser flash photolysis spectroscopic methods. The composite of Acr þ -Mes-incorporated mesoporous silica-alumina with an added copper complex [ðtmpaÞCu II ]ðClO 4 − Þ 2 (tmpa ¼ trisð2-pyridylmethylÞamine) acts as an efficient and robust photocatalyst for the selective oxygenation of p-xylene by molecular oxygen to produce p-tolualdehyde and hydrogen peroxide. Thus, incorporation of Acr þ -Mes into nanosized mesoporous silica-alumina combined with an O 2 -reduction catalyst (½ðtmpaÞCu II 2þ ) provides a promising method in the development of efficient and robust organic photocatalysts for substrate oxygenation by dioxygen, the ultimate environmentally benign oxidant.copper complex catalyst | donor-acceptor dyad | nanosized silica-alumina | p-xylene | photoinduced electron transfer

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mentioning

confidence: 99%

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Fukuzumi

Doi

Itoh

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

119

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“…A new series of ZnP-wire-C 60 conjugates (18)(19)(20), in which co-oligomer bridges incorporating both fluorenes (Fl) and dibenzothiophene-S,S-dioxides (S) are covalently linked to electron-donating ZnP and accepting C 60 , has been synthesized and characterized. The special feature of these systems is that the position of the S units in the co-oligomer linker is systematically varied.…”

Section: Discussionmentioning

confidence: 99%

“…Upon refluxing 12-14 with zinc acetate in chloroform, the corresponding zinc porphyrins ZnP-Ph-Fl-S-CHO 8 (15), ZnP-Ph-S-Fl-CHO (16), and ZnP-Ph-Fl-S-Fl-CHO (17) were obtained as purple powders in high yields. These were then attached to C 60 in the form of fulleropyrrolidines using Prato conditions 82,83 of the in situ generated azomethine ylides, which afforded the target DBAs ZnP-Ph-Fl-S-C 60 (18), ZnPPh-S-Fl-C 60 (19), and ZnP-Ph-Fl-S-Fl-C 60 (20) Chart 1. Model compounds used in this work.…”

Section: Ss-dioxides (S)mentioning

confidence: 99%

“…[12][13][14][15] It is, therefore, of paramount importance to understand the effects of systematically varying the chemical structure and length of the bridge in new DBA systems, where the bridge mediates the electronic coupling between donor-and acceptor moieties over large distances. 4, [16][17][18][19][20][21][22][23][24] Coupling typically decays exponentially with increasing distance between the D and A termini, 25 as reflected by the electron-transfer rate constant k ET . Thus, the rates of charge separation and recombination are characterized by …”

Section: Introductionmentioning

confidence: 99%

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Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates

et al. 2017

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The synthesis of a series of new electron donor−bridge− acceptor (D−B−A) conjugates (18−20) comprising electron-donating zinc(II) porphyrins (ZnPs) and electron-accepting fullerenes (C 60 s) connected through various co-oligomer bridges containing both dibenzothiophene-S,S-dioxide and fluorene units is reported. Detailed investigations using cyclic voltammetry, absorption, fluorescence, and femto/nanosecond transient absorption spectroscopy in combination with quantum chemical calculations have enabled us to develop a detailed mechanistic view of the charge-transfer processes that follow photoexcitation of ZnP, the bridge, or C 60 . Variations in the dynamics of charge separation, charge recombination, and chargetransfer gating are primarily consequences of the electronic properties of the co-oligomer bridges, including their electron affinity and the energy levels of the excited states. In particular, placing one dibenzothiophene-S,S-dioxide building block at the center of the molecular bridge flanked by two fluorene building blocks, as in 20, favors hole rather than electron transfer between the remote electron donors and acceptors, as demonstrated by exciting C 60 rather than ZnP. In 18 and 19, in which one dibenzothiophene-S,S-dioxide and one fluorene building block constitute the molecular bridge, photoexcitation of either ZnP or C 60 results in both hole and electron transfer. Dibenzothiophene-S,S-dioxide is thus shown to be an excellent building block for probing how subtle structural and electronic variations in the bridge affect unidirectional charge transport in D−B−A conjugates. The experimental results are supported by computational calculations.

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“…For example, porphyrin-fullerene linked dyads have been extensively studied, based on the fact that porphyrins play an essential role for charge separation in natural photosynthesis [186,187,188,189,190]. Efficient photo-induced electron transfer to relatively long-lived charge-separated states is observed in such dyads.…”

Section: D2 Optoelectronic Properties Of Fullerene Derivatives Withmentioning

confidence: 99%

Solid State Physicochemical Properties and Applications of Organic and Metallo- Organic Fullerene Derivatives

Mitsari¹,

Romanini²,

Zachariah³

et al. 2016

COC

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Abstract:We review the fundamental properties and main applications of organic derivatives and complexes of fullerenes in the solid-state form. We address in particular the structural properties, in terms of crystal structure, polymorphism, orientational transitions and morphology, and the electronic structure and derived properties, such as chemical activity, electrical conduction mechanisms, optical properties, heat conduction and magnetism. The last two sections of the review focus on the solid-state optoelectronic and electrochemical applications of fullerene derivatives, which range from photovoltaic cells to field-effect transistors and photodetectors on one hand, to electron-beam resists, electrolytes and energy storage on the other.

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ChemInform Abstract: Electronic Communication in Tetrathiafulvalene (TTF)/C₆₀ Systems: Toward Molecular Solar Energy Conversion Materials?

Abstract: Applied chemistry Z 0300Electronic Communication in Tetrathiafulvalene (TTF)/C60 Systems: Toward Molecular Solar Energy Conversion Materials? -[about 40 refs.]. -(MARTIN*, N.; SANCHEZ, L.; HERRANZ, M. A.; ILLESCAS, B.; GULDI, D. M.; Acc. Chem.

Cited by 3 publications

References 1 publication

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates

Solid State Physicochemical Properties and Applications of Organic and Metallo- Organic Fullerene Derivatives

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ChemInform Abstract: Electronic Communication in Tetrathiafulvalene (TTF)/C60 Systems: Toward Molecular Solar Energy Conversion Materials?

Abstract: Applied chemistry Z 0300Electronic Communication in Tetrathiafulvalene (TTF)/C60 Systems: Toward Molecular Solar Energy Conversion Materials? -[about 40 refs.]. -(MARTIN*, N.; SANCHEZ, L.; HERRANZ, M. A.; ILLESCAS, B.; GULDI, D. M.; Acc. Chem.

Cited by 3 publications

References 1 publication

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Formation of a long-lived electron-transfer state in mesoporous silica-alumina composites enhances photocatalytic oxygenation reactivity

Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates

Solid State Physicochemical Properties and Applications of Organic and Metallo- Organic Fullerene Derivatives

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ChemInform Abstract: Electronic Communication in Tetrathiafulvalene (TTF)/C₆₀ Systems: Toward Molecular Solar Energy Conversion Materials?