9 R. C. Haddon, A. S. Perel, R. C. Morris, T. T. M. Palstra,
A. F. Hebard and R. M. Fleming, Appl. Phys. Lett., 1995, 67,
121–123.
10 Y. M. Chen and X. Q. Xiong, Chem. Commun., 2010, 46,
5049–5060.
11 D. A. Tomalia, Prog. Polym. Sci., 2005, 30, 294–324.
12 J. M. J. Fre
3713–3725.
13 B. Helms and E. W. Meijer, Science, 2006, 313, 929–930.
´
chet, J. Polym. Sci., Part A: Polym. Chem., 2003, 41,
14 S. M. Grayson and J. M. J. Fre
3819–3867.
15 J. M. J. Fre
´
chet, Chem. Rev., 2001, 101,
´
chet and D. A. Tomalia, Dendrimers and Other
Dendritic Polymers, Wiley, New York, 2001.
16 V. Percec, J. G. Rudick, M. Peterca, M. Wagner, M. Obata,
C. M. Mitchell, W. D. Cho, V. S. K. Balagurusamy and
P. A. Heiney, J. Am. Chem. Soc., 2005, 127, 15257–15264.
17 A. Zhang, L. Okrasa, T. Pakula and A. D. Schluter, J. Am. Chem.
Soc., 2004, 126, 6658–6666.
¨
18 W.-S. Li, D.-L. Jiang and T. Aida, Angew. Chem., Int. Ed., 2004,
43, 2943–2947.
19 B. Helms, J. L. Mynar, C. J. Hawker and J. M. J. Fre
Chem. Soc., 2004, 126, 15020–15021.
´
chet, J. Am.
Fig. 3 (a) J–V characteristics of polymer solar cells under AM 1.5
condition (100 mW cmꢀ2). (b) IPCE of P3HT/fullerene-rich dendron
and P3HT/fullerene-rich linear polymer. AFM height images of P3HT
blend with (c) fullerene-rich dendron and (d) fullerene-rich linear
polymer.
20 A. D. Schluter and J. P. Rabe, Angew. Chem., Int. Ed., 2000, 39,
¨
864–883.
21 H. Frey, Angew. Chem., Int. Ed., 1998, 37, 2193–2197.
22 U. Hahn, J.-F. Nierengarten, F. Vogtle, A. Listorti, F. Monti and
¨
N. Armaroli, New J. Chem., 2009, 33, 337–344.
23 U. Hahn, F. Cardinali and J.-F. Nierengarten, New J. Chem., 2007,
31, 1128–1138.
quantum efficiencies, shown in the inset to Fig. 3b, exhibit only
B35% for P3HT/fullerene-rich dendron and only B15% for
P3HT/fullerene-rich linear polymer at a broad peak centered
at 530 nm, which implies that charge separation, transporta-
tion, and collection of the device are inefficient and photons
absorbed by the active layers are inefficiently converted into
electricity.
´
24 T. M. Figueira-Duarte, A. Gegout and J.-F. Nierengarten, Chem.
Commun., 2007, 109–119.
25 D. Bonifazi, A. Kiebele, M. Stohr, F. Y. Cheng, T. Jung,
F. Diederich and H. Spillmann, Adv. Funct. Mater., 2007, 17,
1051–1062.
26 N. Martin, Chem. Commun., 2006, 2093–2104.
27 J.-F. Nierengarten, New J. Chem., 2004, 28, 1177–1191.
28 D. M. Guldi, A. Swartz, C. P. Luo, R. Gomez, J. L. Segura and
N. Martin, J. Am. Chem. Soc., 2002, 124, 10875–10886.
29 T. Chuard and R. Deschenaux, J. Mater. Chem., 2002, 12,
1944–1951.
30 A. Hirsch and O. Vostrowsky, Top. Curr. Chem., 2001, 217, 51–93.
´
31 K. L. Wooley, C. J. Hawker, J. M. J. Frechet, F. Wudl,
G. Srdanov, S. Shi, C. Li and M. Kao, J. Am. Chem. Soc., 1993,
115, 9836–9837.
32 U. Hahn, J. J. Gonzalez, E. Huerta, M. Segura, J.-F. Eckert,
´
In summary, we have successfully prepared a fullerene-rich
dendron based on norbornene-type monomer at the focal point
by the esterification of dendritic alcohol with an acyl chloride
functionalized C60. Upon applying a combination of ROMP
strategy and a controlled methodology of a progressive addition
of catalyst, we have established a platform for the synthesis
of a fullerene-rich linear polymer. Despite some remarkable
recent achievements based on the dendritic frameworks, it is
clear that the example discussed herein represents only the first
steps towards the design of fullerene-rich linear polymer.
This work was supported by the Basic Science Research
Program through the National Research Foundation of Korea
(NRF) (2010-0002494), (2010-0019408), (2010-0026916),
(2010-0026163), and (NRF-2009-C1AAA001-0093020) as well
as the MC-CAM of UCSB.
F. Cardinali, J. de Mendoza and J.-F. Nierengarten, Chem.–Eur.
J., 2005, 11, 6666–6672.
33 J.-F. Nierengarten, Top. Curr. Chem., 2003, 228, 87–110.
34 S. Rajaram, T.-L. Choi, M. Rolandi and J. M. J. Fre
Chem. Soc., 2007, 129, 9619–9621.
´
chet, J. Am.
35 J. S. Moore and S. I. Stupp, Macromolecules, 1990, 23, 65–70.
36 T.-L. Choi and R. H. Grubbs, Angew. Chem., Int. Ed., 2003, 42,
1743–1746.
37 J. A. Love, J. P. Morgan, T. M. Trnka and R. H. Grubbs, Angew.
Chem., Int. Ed., 2002, 41, 4035–4037.
38 A. D. Schluter, C. R. Chim., 2003, 6, 843–851.
¨
´
39 M. Yoshida, Z. M. Fresco, S. Ohnishi and J. M. J. Frechet,
Macromolecules, 2005, 38, 334–344.
40 M. B. Runge, S. Dutta and N. B. Bowden, Macromolecules, 2006,
39, 498–508.
Notes and references
1 C. Yang, S. Cho, A. J. Heeger and F. Wudl, Angew. Chem., Int.
Ed., 2009, 48, 1592–1595.
41 M. G. Nava, S. Setayesh, A. Rameau, P. Masson and
J. F. Nierengarten, New J. Chem., 2002, 26, 1584–1589.
2 Y. Matsuo and E. Nakamura, Chem. Rev., 2008, 108, 3016–3028.
3 C. Yang, J. Y. Kim, S. Cho, J. K. Lee, A. J. Heeger and F. Wudl,
J. Am. Chem. Soc., 2008, 130, 6444–6450.
42 A. Kraus and K. Mullen, Macromolecules, 1999, 32, 4214–4219.
43 M. Schappacher, J. L. Putaux, C. Lefebvre and A. Deffieux, J. Am.
Chem. Soc., 2005, 127, 2990–2998.
¨
4 B. C. Thompson and J. M. J. Fre
2008, 47, 58–77.
´
chet, Angew. Chem., Int. Ed.,
44 M. Schappacher and A. Deffieux, Macromolecules, 2005, 38,
7209–7213.
5 F. Wudl, Acc. Chem. Res., 1992, 25, 157–161.
6 N. F. Steinmetz, V. Hong, E. D. Spoerke, P. Lu, K. Breitenkamp,
M. G. Finn and M. Manchester, J. Am. Chem. Soc., 2009, 131,
17093–17095.
7 S. Gunes, H. Neugebauer and N. S. Sariciftci, Chem. Rev., 2007,
¨
107, 1324–1338.
45 S. S. Sheiko, M. da Silva, D. Shirvaniants, I. LaRue,
S. Prokhorova, M. Moeller, K. Beers and K. Matyjaszewski,
J. Am. Chem. Soc., 2003, 125, 6725–6728.
46 K. Matyjaszewski, S. H. Qin, J. R. Boyce, D. Shirvanyants and
S. S. Sheiko, Macromolecules, 2003, 36, 1843–1849.
47 H. Zhang, P. C. M. Grim, P. Foubert, T. Vosch, P. Vanoppen,
8 K. M. Coakley and M. D. McGehee, Chem. Mater., 2004, 16,
4533–4542.
U. M. Wiesler, A. J. Berresheim, K. Mullen and F. C. De Schryver,
¨
Langmuir, 2000, 16, 9009–9014.
c
3080 Chem. Commun., 2011, 47, 3078–3080
This journal is The Royal Society of Chemistry 2011