Efficient electron transfer in β-substituted porphyrin-C60 dyads connected through a p-phenylenevinylene dimer

被引：28

作者：

Santos, Jose ^{[1
]}

Illescas, Beatriz M. ^{[1
]}

Wielopolski, Mateusz ^{[2
,3
]}

Silva, Ana M. G. ^{[4
]}

Tome, Augusto C. ^{[4
]}

Guldi, Dirk M. ^{[2
,3
]}

Martin, Nazario ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain

[2] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91058 Erlangen, Germany

[3] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat, D-91058 Erlangen, Germany

[4] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal

来源：

TETRAHEDRON | 2008年 / 64卷 / 50期

关键词：

D O I：

10.1016/j.tet.2008.09.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new porphyrin-C-60 dyads have been synthesized in which the electroactive moieties have been connected through a p-phenylenevinylene dimer. The electrochemical Study confirms the amphoteric redox behavior of these dyads. Irradiation of these compounds gives rise to the corresponding radical pair confirming that substitution on the beta-position of the porphyrin facilitates the electronic communication between the porphyrin and C-60. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：11404 / 11408

页数：5

共 24 条

[1] Synthesis, electronic characterisation and significant second-order non-linear optical responses of meso-tetraphenylporphyrins and their ZnII complexes carrying a push or pull group in the β pyrrolic position [J].

Annoni, E ;

Pizzotti, M ;

Ugo, R ;

Quici, S ;

Morotti, T ;

Bruschi, M ;

Mussini, P .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (19) :3857-3874

[2] Tuning electron transfer through p-phenyleneethynylene molecular wires [J].

Atienza, Carmen ;

Martin, Nazario ;

Wielopolski, Mateusz ;

Haworth, Naomi ;

Clark, Timothy ;

Guldi, Dirk M. .

CHEMICAL COMMUNICATIONS, 2006, (30) :3202-3204

[3] Determination of the attenuation factor in fluorene-based molecular wires [J].

Atienza-Castellanos, Carmen ;

Wielopolski, Mateusz ;

Guldi, Dirk M. ;

van der Pol, Cornelia ;

Bryce, Martin R. ;

Filippone, Salvatore ;

Martin, Nazario .

CHEMICAL COMMUNICATIONS, 2007, (48) :5164-5166

[4] Probing the donor-acceptor proximity on the physicochemical properties of porphyrin-fullerene dyad: "Tail-on" and "tail-off" binding approach [J].

D'Souza, F ;

Deviprasad, GR ;

El-Khouly, ME ;

Fujitsuka, M ;

Ito, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5277-5284

[5] Electronic interactions and photoinduced electron transfer in covalently linked porphyrin-C60(pyridine) diads and supramolecular triads formed by self-assembling the diads and zinc porphyrin [J].

D'Souza, F ;

Deviprasad, GR ;

Zandler, ME ;

El-Khouly, ME ;

Fujitsuka, M ;

Ito, O .

JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (19) :4952-4962

[6] Spectroscopic, electrochemical, and photochemical studies of self-assembled via axial coordination zinc porphyrin-fulleropyrrolidine dyads [J].

D'Souza, F ;

Deviprasad, GR ;

Zandler, ME ;

Hoang, VT ;

Klykov, A ;

VanStipdonk, M ;

Perera, A ;

El-Khouly, ME ;

Fujitsuka, M ;

Ito, O .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (13) :3243-3252

[7] Molecular-wire behaviour in p-phenylenevinylene oligomers [J].

Davis, WB ;

Svec, WA ;

Ratner, MA ;

Wasielewski, MR .

NATURE, 1998, 396 (6706) :60-63

[8] Electronic communication through π-conjugated wires in covalently linked porphyrin/C60 ensembles [J].

de la Torre, G ;

Giacalone, F ;

Segura, JL ;

Martín, N ;

Guldi, DM .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (04) :1267-1280

[9] Electrochemistry of fullerenes and their derivatives [J].

Echegoyen, L ;

Echegoyen, LE .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (09) :593-601

[10] Photocurrent generation in thin SnO2 nanocrystalline semiconductor film electrodes from photoinduced charge-separation state in porphyrin-C60 dyad [J].

Fungo, F ;

Otero, L ;

Borsarelli, CD ;

Durantini, EN ;

Silber, JJ ;

Sereno, L .

JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (16) :4070-4078

← 1 2 3 →