ORGANIC
LETTERS
2008
Vol. 10, No. 21
4979-4982
First Triazole-Linked
Porphyrin-Fullerene Dyads
Michael A. Fazio,* Olivia P. Lee, and David I. Schuster*
Department of Chemistry, New York UniVersity, New York, New York 10003
Received September 2, 2008
ABSTRACT
A general procedure for the synthesis of 1,2,3-triazole-linked porphyrin-fullerene dyads is described. Four of these compounds have been
prepared and characterized.
Porphyrin-fullerene dyads have been studied extensively
with respect to photoinduced energy or electron transfer rates
and mechanisms.1 Face-to-face distances and the nature of
the bridge that links the two chromophores have been
subjects of investigation since these properties have such a
large influence over the dynamics of electron and energy
transfer processes.2 The bridging unit in porphyrin-fullerene
dyads performs two functions: it acts as a conduit through
which electron transfer is facilitated, and it serves to orient
the two chromophores at set distances and bond angles. In
this paper, we report the use of a 1,4-diphenyl-1,2,3-triazole
linker to connect a porphyrin and fullerene. The recent
popularity of “click” reactions3 has led to examples of
porphyrin triazoles4 and fullerene triazoles,5 but to the best
ofourknowledge,noexamplesoftriazole-linkedporphyrin-fullerene
dyads have been reported.
Imahori et al.2b demonstrated that in dyads with conjugated
linkers electron transfer (ET) is promoted upon photoexci-
tation through bonds via a superexchange interaction, and
they investigated the effect of ortho, meta, and para con-
nectivity on the dynamics of photoinduced ET. Our triazole
linker has two phenyl groups through which the chro-
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Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223. (c) D´ıez-
Gonza´les, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem.-Eur. J. 2006,
12, 7558. (d) Wu, P.; Fokin, V. V. Aldrichimica Acta 2007, 40, 7.
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¨
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therein. (b) Bracher, P. J.; Schuster, D. I. Fullerenes: From Synthesis to
Optoelectronic Properties; Guldi, D. M., Martin, N., Eds.; Kluwer Academic
Publishers: Dordrecht, 2002; pp 163-212. (c) Xiao, S.; Li, Y.; Li, Y.;
Zhuang, J.; Wang, N.; Liu, H.; Ning, B.; Liu, Y.; Lu, F.; Fan, L.; Yang,
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Mater. 2007, 19, 5194. (b) Isobe, H.; Cho, K.; Solin, N.; Werz, D. B.;
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Macromolecules 2008, 41, 515.
(2) (a) Guldi, D. M.; Luo, C.; Prato, M.; Troisi, A.; Zerbetto, F.;
Scheloske, M.; Dietel, E.; Bauer, W.; Hirsch, A. J. Am. Chem. Soc. 2001,
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10.1021/ol802053k CCC: $40.75
Published on Web 10/11/2008
2008 American Chemical Society