6
Tetrahedron
1H, HC(3)GABA), 2.10-2.01 (m, 1H, HC(3)GABA), 1.92-1.72 (m,
Yau, H. C.; Bayazit, M. K.; Steinke, J. H. G.; Shaffer, M. S. P.
ACCEPTED MANUSCRIPT
4H, H2C(2)hexyl, H2C(3)hexyl), 1.61-1.50 (m, 4H, CH2(5)hexyl
CH2(4)hexyl ppm; 13C NMR (125 MHz, CDCl3): 172.96
,
Macromolecules 2014, 47, 4870−4875
.
2. (a) Voroshazi, E.; Vasseur, K.; Aernouts, T.; Heremans, P.;
Baumann, A.; Deibel, C.; Xue, X.; Herring, A.J.; Athans, A. J.;
)
(COGABA), 168.19 (COGly), 154.11, 153.76, 153.47, 153.37,
152.31, 151.84, 150.86, 150.12, 150.04, 149.46, 149.16, 148.58,
148.48, 148.38, 148.15, 147.39, 147.29, 147.06, 146.99, 146.26,
146.12, 146.07, 145.74, 145.63, 144.59, 144.53, 144.35, 142.80,
142.53, 142.49, 142.45, 142.28, 141.92, 141.53, 141.48, 141.44,
141.38, 141.33, 138.91, 138.46, 136.04, 135.84, 135.33, 135.22,
131.33, 131.24 (sp2 Cfull), 69.80, 69.41, 69.24, 69.17 (sp3 Cfull),
Lada, T. A.; Richter, H.; Rand, B. P. J. Mater. Chem. 2011, 21
17345−17352; (b) Zhou, S.; Ouyang, J.; Golas, P.; Wang, F.; Pan,
Y. J. Phys. Chem. B 2005, 109, 19741−19747
3. (a) Beulen, M. W. J.; Rivera, J. A.; Herranz, M. A.; Illescas, B.;
Martín, N.; Echegoyen, L. J. Org. Chem. 2001, 66, 4393−4398
(b) Lu, Q.; Schuster, D. I.; Wilson, S. R. J. Org. Chem. 1996, 61
,
.
;
,
4764−4768; (c) Kordatos, K.; Bosi, S.; Da Ros, T.; Zambon, A.;
Lucchini, V.; Prato, M. J. Org. Chem. 2001, 66, 2802−2808; (d)
Djojo, F.; Herzog, A.; Lamparth, I.; Hampel, F.; Hirsch, A. Chem.
68.50(CH2pyrr-1), 67.62(CH2pyrr-2), 67.07(CH2pyrr-2), 66.69 (CH2
pyrr-
1), 54.00 (CH2(1)hexyl), 51.93 (CH2(4)GABA), 43.13 (CH2Gly), 39.23
(CH2(6)hexyl), 34.75 (CH2(2)GABA), 29.35 (CH2(5)hexyl), 27.06
(CH2(2)hexyl), 26.24 (CH2(3)hexyl), 25.47 (CH2(4)hexyl), 22.80
(CH2(3)GABA) ppm; Key HMBC correlations: 3.70d/51.93 (Hpyrr-
2/C(4)GABA), 3.57d; 3.84d/54.00 (Hpyrr-1/C(1)hexyl); MS (ESI):
Calculated for C76H32N4O2 (M+2H)2+: 516.1257, (M+H)+:
1031.2442, found 516.1254, 1031.2438; UV (CH2Cl2): λmax(ε):
264 (35000), 308 (18000), 638 (290), 705 (200) nm (mol-
1dm3cm-1).
Eur. J. 1996, 2, 1537−1547.
4. (a) Zhang, B.; Subbiah, J.; Lai, Y-Y.; White, J. M.; Jones, D. J.;
Wong, W. W. H. Chem. Commun. 2015, 51, 9837−9840; (b) Tao,
R.; Umeyama, T.; Higashino, T.; Koganezawa, T.; Imahori, H.
Chem. Commun. 2015, 51, 8233−8236; (c) Meng, X.; Zhao, G.;
Xu, Q.; Tan, Z.; Zhang, Z.; Jiang, L.; Shu, C.; Wang, C.; Li, Y.
Adv. Funct. Mater. 2014, 24, 158−163
5. Wilson, S. R.; Lu, Q. Tetrahedron Lett. 1995, 36, 5707−5710
6. (a) Isaacs, L.; Haldimann, R. F.; Diederich, F. Angew Chem Int
Ed. 1994, 33 2339−2342 (b) Isaacs, L.; Diederich, F.;
Haldimann, R. F. Helv. Chim. Acta 1997, 80, 317−342
7. (a) Thilgen, C.; Diederich, F. C. R. Chimie 2006, , 868−880; (b)
.
.
,
;
.
4.4.4. Bisadduct 17d (cis-2): IR(ATR): 3308, 2930, 2858,
9
1
2788, 1656, 1531, 1449, 1343, 1237, 1163, 1116 cm-1; H NMR
Sergeyev, S.; Schär, M.; Seiler, P.; Lukoyanova, E.; Echegoyen,
L.; Diederich, F. Chem. Eur. J. 2005, 11, 2284−2294; (c)
Nierengarten, J-F.; Gramlich, V.; Cardullo, F.; Diederich, F.
Angew. Chem., Int. Ed. Engl. 1996, 35, 2101−2103; (d) Sutton, L.
R.; Scheloske, M.; Pirner, K. S.; Hirsch, A.; Guldi, D. M.;
(500 MHz, CDCl3): 6.93 (t, J=5.2 Hz, 1H, NHGly), 6.00 (t, J=6.0
Hz, 1H, NHhexyl), 4.36 (d, J=9 Hz, 1H, HCpyrr-2), 4.23 (d, J=8.5
Hz, 1H, HCpyrr-1), 4.11 (dd, J=6.5 Hz, 16.5 Hz, 1H, HCGly), 3.96
(d, J=9.0 Hz, 1H, HCpyrr-2), 3.95 (d, J=9.0 Hz, 1H, HCpyrr-1), 3.87
(d, J=9.0 Hz, 1H, HCpyrr-2), 3.76 (dd, J=4.0; 16.0 Hz, 1H, HCGly),
3.73 (d, 1H, J=9.0 Hz, HCpyrr-1), 3.72 (d, J=9.0 Hz, 1H, HCpyrr-2),
3.58 (d, J=9.0 Hz, 1H, HCpyrr-1), 3.47-3.38 (m, 1H, HC(6)hexyl),
3.10-3.01 (m, 2H, HC(6)hexyl, HC(4)GABA), 3.01-2.96 (m, 1H,
HC(1)hexyl), 2.96-2.90 (m, 1H, HC(4)GABA), 2.78-2.71 (m, 1H,
HC(1)hexyl), 2.62 (dt, J=13.5, 7.0 Hz, 1H, HC(2)GABA), 2.47 (dt,
J=13.5, 6.0 Hz, 1H, HC(2)GABA), 2.10 (quint, J=6.5 Hz, 2H,
H2C(3)GABA), 1.93-1.83 (m, 1H, HC(2)hexyl), 1.82-1.74 (m, 1H,
HC(3)hexyl), 1.74-1.67 (m, 1H, HC(2)hexyl), 1.67-1.61 (m, 2H, H2
C(5)hexyl ), 1.57-1.42 (m, 3H, HC(3)hexyl, H2C(4)hexyl) ppm; 13C
NMR (125 MHz, CDCl3): 173.72 (COGABA), 168.72 (COGly),
158.61, 158.37, 156.76, 156.59, 149.32, 148.85, 148.77, 148.38,
148.01, 147.93, 147.87, 147.54, 147.47, 147.20, 147.16, 146.99,
146.91, 146.49, 146.14, 146.10, 145.82, 145.73, 145.54, 145.43,
145.13, 145.12, 144.89, 144.64, 144.55, 144.53, 144.22, 144.03,
142.92, 141.70, 141.65, 140.99, 139.09, 138.88, 133.90, 133.38,
Gisseelbrecht, J-P. J. Am. Chem. Soc. 2004, 126, 10370−10381
(e) Bourgeois, J-P.; Echegoyen, L.; Fibbioli, M.; Pretsch, E.;
Diederich, F. Angew. Chem., Int. Ed. 1998, 37, 2118−2121
8. Zhang, B.; White, J. M.; Jones, D. J.; Wong, W. W. H. Org.
Biomol. Chem. 2015, 13, 10505−10510
9. (a) Smith, P. M.; McCarty, A. L.; Nguyen, N. Y.; Zandler, M. E.;
D’Souza, F. Chem. Commun. 2003, 1754−1755; (b) Rotas, G.;
Tagmatarchis, N. Tetrahedron Lett. 2009, 50, 398–401; (c)
Iglesias, R. S.; Claessens, C. G.; Torres, T.; Rahman, G. M. A.;
Guldi, D. M. Chem. Commun. 2005, 2113−2115; (d) Zhou, Z.;
;
.
.
Schuster, D. I.; Wilson, S. R. J. Org. Chem. 2006, 71, 1545−1551
10. Chronakis, N.; Hirsch, A. C. R. Chimie 2006, , 862-867.
11. Bottari, G.; Trukhina, O.; Kahnt, A.; Frunzi, F.; Murata, Y.;
Rodríguez-Fortea, A.; Poblet, J. M.; Guldi, D. M.; Torres, T.
.
9
Angew. Chem., Int. Ed. 2016, 55, 11020−11025
12. Kop, T.; Bjelaković, M.; Milić, D. Tetrahedron 2015, 71
4801−4809
13. Kop, T.; Bjelaković, M.; Đorđević, J.; Žekić, A.; Milić, D. RSC
Adv. 2015, , 94599−94606
.
,
.
5
.
pyrr-
133.26, 132.80, 129.18 (sp2 Cfull), 67.98 (CH2pyrr-2), 67.77 (CH2
14. (a) Babu, S. S.; Möhwald, H.; Nakanishi, T. Chem. Soc. Rev.
2010, 39, 4021−4035; (b) Guldi, D. M.; Zerbetto, F.; Georgakilas,
1), 67.14, 66.95, 66.74, 66.68 (sp3 Cfull), 66.52 (CH2pyrr-1), 65.88
(CH2pyrr-2), 53.81 (CH2(1)hexyl), 52.02 (CH2(4)GABA), 43.30
(CH2Gly)), 39.36 (CH2(6)hexyl), 33.86 (CH2(2)GABA), 28.15
(CH2(5)hexyl), 26.85 (CH2(2)hexyl), 25.39 (CH2(4)hexyl), 25.21
(CH2(3)hexyl), 24.28 (CH2(3)GABA) ppm; Key HMBC correlations:
3.73d/53.81 (Hpyrr-1/C(1)hexyl), 3.57d/53.81 (Hpyrr-1/C(1)hexyl),
3.87d/52.02 (Hpyrr-2/C(4)GABA), 3.72d/52.01 (Hpyrr-2/C(4)GABA); MS
(ESI): Calculated for C76H32N4O2 (M+2H)2+: 516.1257, (M+H)+:
1031.2442, found 516.1254, 1031.2426; UV (CH2Cl2): λmax(ε):
259 (17000), 305 (8200), 446 (1000) nm (mol-1dm3cm-1).
V.; Prato, M. Acc. Chem. Res. 2005, 38, 38−43
15. Bjelaković, M. S.; Kop, T. J.; Vlajić, M.; Đorđević, J.; Milić, D.
R. Tetrahedron 2014, 70, 8564−8570
.
.
Supplementary Material
Detailed reaction procedures for the syntheses of compounds
2-14 with their spectra, as well as Table S1 (NMR chemical
shifts of bisadducts 17) and spectra (IR, 1H and 13C NMR,
COSY, HSQC, HMBC, MS, and UV-Vis) for fulleropyrrolidine
monoadducts (15 and 16) and bisadducts (17a-d) are given in the
Supplementary Information.
Acknowledgments
This research has been supported by Serbian Ministry of
Education, Science and Technological Development, grant
172002.
References and notes
1. (a) Nakamura, Y.; Kato, S-I. Chem. Rec. 2011, 11, 77−94; (b)
Zhou, Z.; Wilson, S. R. Curr. Org. Chem. 2005,
Hirsch, A. Chem. Rec. 2005, , 196−208; (d) Thilgen, C.;
Sergeyev, S.; Diederich, F. Top. Curr. Chem. 2004, 248, 1−61; (e)
9, 789−811; (c)
5