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Synlett 2006(18): 3095-3099  
DOI: 10.1055/s-2006-947327
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Excited-State Properties of an Oligophenylenevinylene Heptamer Substituted with Two Fullerene Moieties

Aline Gégouta, Teresa M. Figueira-Duartea, Jean-François Nierengarten*a, Andrea Listortib, Nicola Armaroli*b
a Groupe de Chimie des Fullerènes et des Systèmes Conjugués, Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
Fax: +33(5)61553003; e-Mail: jfnierengarten@lcc-toulouse.fr;
b Istituto per la Sintesi Organica e la Fotoreattività, Molecular Photoscience Group, Consiglio Nazionale delle Ricerche, Via Gobetti 101, 40129 Bologna, Italy
Fax: +39(051)6399844; e-Mail: armaroli@isof.cnr.it;
Further Information

Publication History

Received 7 April 2006
Publication Date:
04 August 2006 (online)

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Abstract

An oligophenylenevinylene (OPV) derivative substituted with two fullerene subunits has been prepared starting from a fullerene carboxylic acid derivative and an OPV heptamer bearing two alcohol functions. Photophysical investigations have revealed the occurrence of intramolecular photoinduced energy- and electron-transfer processes in this hybrid compound.

Key words

fullerene - conjugated system - energy transfer - electron transfer - singlet oxygen

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12

Compound 17: 1H NMR (300 MHz, CDCl3): δ = 7.69 (s, 2 H), 7.48 (m, 16 H), 7.32 (d, 3 J = 16.0 Hz, 2 H), 7.15 (d, 3 J = 16.0 Hz, 2 H), 7.08 (s, 4 H), 7.04 (d, 3 J = 16.0 Hz, 2 H), 6.94 (d, 3 J = 16.0 Hz, 2 H), 6.72 (s, 4 H), 6.57 (d, 4 J = 1.5 Hz, 4 H), 6.38 (t, 4 J = 1.5 Hz, 2 H), 5.44 (s, 4 H), 5.39 (s, 4 H), 5.02 (s, 4 H), 4.03 (t, 3 J = 6.5 Hz, 8 H), 3.98 (t, 3 J = 6.5 Hz, 4 H), 3.85 (t, 3 J = 6.5 Hz, 8 H), 1.80 (m, 20 H), 1.32 (m, 180 H), 0.87 (2t, 3 J = 6.0 Hz, 30 H). 13C NMR (75 MHz, CDCl3): δ = 166.9, 163.4, 163.3, 160.9, 153.7, 145.6, 145.55, 145.5, 145.4, 145.35, 145.3, 145.0, 144.9, 144.85, 144.2, 143.4, 143.3, 142.5, 141.25, 141.2, 127.8, 127.4, 127.3, 127.1, 107.7, 105.7, 102.0, 73.9, 71.6, 69.6, 69.5, 68.6, 63.1, 51.7, 32.4, 30.8, 30.15, 30.1, 29.9, 29.8, 29.7, 26.6, 23.1, 14.6, 14.5. IR (ATR): 1702 (C=O). MS (MALDI-TOF): 4501 [MH+]. Anal. Calcd for C320H302O22: C, 85.41; H, 6.76. Found: C, 85.68; H, 6.73.