ORGANIC
LETTERS
2002
Vol. 4, No. 3
335-338
Energy Transfer Processes in Novel
Subphthalocyanine−Fullerene
Ensembles
,†
,‡
David Gonza´lez-Rodr´ıguez,† Toma´s Torres,* Dirk M. Guldi,* Jose´ Rivera,§,| and
Luis Echegoyen*
,§
Departamento de Qu´ımica Orga´nica (C-I), Facultad de Ciencias, UniVersidad
Auto´noma de Madrid, Cantoblanco 28049 Madrid, Spain, Radiation Laboratory,
UniVersity of Notre Dame, Notre Dame, Indiana 46556, and Department of Chemistry,
UniVersity of Miami, Coral Gables, Florida 33124
Received October 11, 2001
ABSTRACT
A series of subphthalocyanine−C dyads in which the two subunits are placed at different distances have been prepared and their electrochemical
60
properties measured. Photophysical measurements reveal energy transfer events following the initial photoexcitation of the subphthalocyanine
chromophore.
Subphthalocyanines1 (SubPcs) are nonplanar2 aromatic mac-
rocycles that differ from their higher homologues, phthalo-
cyanines,3 in that they comprise three isoindole units around
a boron atom. Whereas SubPcs have shown very interesting
photophysical properties,2e,4 their ability to promote intramo-
lecular charge or energy transfer processes, when included
in electroactive dyads, remains unexplored. Regarding the
design of novel photo- and electroactive donor-acceptor
* Other corresponding authors. E-mail (D.G.): guldi.1@nd.edu. E-mail
(L.E.): echegoyen@miami.edu.
† Universidad Auto´noma de Madrid.
‡ University of Notre Dame.
§ University of Miami.
(3) (a) Phthalocyanines: Properties and Applications; Leznoff, C. C.;
Lever, A. B. P., Eds.; VCH: Weinheim, 1989, 1993, 1996; Vols 1-4. (b)
Hanack, M.; Heckman, H.; Polley, R. In Methods in Organic Chemistry
(Houben-Weyl); Schauman, E., Ed.; Georg Thieme Verlag: Stuttgart, 1998;
Vol. E 94, p 717. (c) de la Torre, G.; Nicolau, M.; Torres, T. In
Phthalocyanines: Syntheses, Supramolecular Organization and Physical
Properties (Supramolecular PhotosensitiVe and ElectroactiVe Materials);
Nalwa, H. S., Ed.; Academic Press: New York, 2001; pp 1-111.
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Nonell, S.; Mart´ı, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc.
1998, 120, 12808-12817. (b) Sastre, A.; Torres, T.; Diaz-Garcia, M. A.;
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Chem. Soc. 1996, 118, 2746-2747. (c) Kitagawa, S.; Shinkai, M.; Nanba,
N.; Yoshimura, E. E. Jpn. Kokai Tokyo Koho JP 09,131,968 [97,131,968],
1997; Chem. Abstr. 1997, 127, 1277.
| Department of Chemistry, Pontificial Catholic University, Ponce, Puerto
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B.; Sastre, A.; Torres, T. Synthesis 1996, 1139-1151. (b) Claessens, C.
G.; Gonza´lez-Rodr´ıguez, D.; Torres, T. Chem. ReV. 2002, in press.
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10.1021/ol0169022 CCC: $22.00 © 2002 American Chemical Society
Published on Web 01/05/2002