Self-assembly and optical properties of hydrogen bonded nanostructures containing C60 and pyrene

Carbon

Volumn 44, Issue 13, 2006, Pages 2785-2792

  Xiao, Jinchong ^a,b   Liu, Yang ^a   Li, Yongjun ^a,b   Ye, JianPing ^c   Li, Yuliang ^a   Xu, Xinhe ^a,b   Li, Xiaofang ^a   Liu, Huibiao ^a   Huang, Changshui ^a,b   Cui, Shuang ^a,b   Zhu, Daoben ^a  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c INSTITUTE OF CHEMISTRY   (China)

Author keywords

Aggregation; Fullerene; Scanning electron microscopy

Indexed keywords

FULLERENES; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCURRENTS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY;

BARBITURIC ACID-SUBSTITUTED FULLERENE DERIVATIVE; DIPYRENEMETHYL-SUBSTITUTED MELAMINE; HYDROGEN BONDED NANOSTRUCTURES;

NANOSTRUCTURED MATERIALS;

EID: 33748078770     PISSN: 00086223     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbon.2006.03.031     Document Type: Article

References (48)

1. 60 fullerene derivatives. Acc Chem Res 33 (2000) 695-703
2. Reed C.A., and Bolskar R.D. Discrete fulleride anions and fullerenium cations. Chem Rev 100 (2000) 1075-1120
3. Imahori H., Norieda H., Yamada H., Nishimura Y., Yamazaki I., Sakata Y., et al. Light-harvesting and photocurrent generation by gold electrodes modified with mixed self-assembled monolayers of boron-dipyrrin and ferrocene-porphyrin-fullerene triad. J Am Chem Soc 123 (2001) 100-110
4. McClenaghan N.D., Absalon C., and Bassani D.M. Facile synthesis of a fullerene-barbituric acid derivative and supramolecular catalysis of its photoinduced dimerization. J Am Chem Soc 125 (2003) 13004-13005
5. Sessler J.L., Jayawickramarajah J., and Sathiosatham M. In: Steed J.W., and Atwood J.L. (Eds). Encyclopedia of supramolecular chemistry (2004), Marcel Dekker, NY 535-545
6. Prato M., and Maggini M. Fulleropyrrolidines: a family of full-fledged fullerene derivatives. Acc Chem Res 31 (1998) 519-526
7. Lehn J.M. Supramolecular chemistry-scope and perspectives molecules, supermolecules devices. Angew Chem Int Ed 27 (1988) 89-112
8. Whitesides G.M., Simanek E.E., Mathias J.P., Seto C.T., Chin D.N., Mammen M., et al. Noncovalent synthesis: using physical-organic chemistry to make aggregates. Acc Chem Res 28 (1995) 37-44
9. Garcia-Tellado F., Geib S.J., Goswami S., and Hamilton A.D. Molecular recognition in the solid state: controlled assembly of hydrogen-bonded molecular sheets. J Am Chem Soc 113 (1991) 9265-9269
10. Hahn U., Gonzlez J.J., Huerta E., Segura M., Eckert J.F., Cardinali F., et al. A highly directional fourfold hydrogen-bonding motif for supramolecular structure though self-assembly of fullerodendimers. Chem Eur J 11 (2005) 6666-6672
11. Prins L.J., Reinhoudt D.N., and Timmerman P. Nonvalent synthesis using hydrogen bonding. Angew Chem Int Ed 40 (2001) 2382-2426
12. Sijbesma R.P., and Meijer E.W. Quadruple hydrogen bonded systems. Chem Commun (2003) 5-16
13. Timmerman P., and Prins L.J. Noncovalent synthesis of melamine-cyanuric/barbituric acid derived nanostructures: region- and stereoselection. Eur J Org Chem (2001) 3191-3205
14. Drain C.M., Russell K.C., and Lehn J.M. Self-assembly of a multi-porphyrin supramolecular macrocycle by hydrogen bond molecular recognition. Chem Commun (1996) 337-338
15. Kawasaki T., Tokuhiro M., Kimizuka N., and Kunitake T. Hierarchical self-assembly of chiral complementary hydrogen-bond networks in water: reconstitution of supramolecular membranes. J Am Chem Soc 123 (2001) 6792-6800
16. Ranganathan A., Pedireddi V.R., and Rao C.N.R. Hydrothermal synthesis of organic channel structures: 1:1 hydrogen-bonded adducts of melamine with cyanuric and trithiocyanuric acids. J Am Chem Soc 121 (1999) 1752-1753
17. Yagai S., Karatsu T., and Kitamura A. Photoresponsive melamine barbiturate hydrogen-bonded assembly. Chem Commun (2003) 1844-1845
18. Mathias J.P., Simanek E.E., and Whitesides G.M. Self-assembly through hydrogen bonding: peripheral crowding-a new strategy for the preparation of stable supramolecular aggregates based on parallel, connected CA3-M3 rosettes. J Am Chem Soc 116 (1994) 4326-4340
19. Bielejewska A.G., Marjo C.E., Prins L.J., Timmerman P., De Jong F., and Reinhoudt D.N. Thermodynamic stabilities of linear and crinkled tapes and cyclic rosettes in melamine-cyanurate assemblies: a model description. J Am Chem Soc 123 (2001) 7518-7533
20. Seto C.T., and Whitesides G.M. Molecular self-assembly through hydrogen bonding: supramolecular aggregates based on the cyanuric acid-melamine lattice. J Am Chem Soc 115 (1993) 905-916
21. Shi Z.Q., Li Y.L., Gong H.F., Liu M.H., Xiao S.X., Liu H.B., et al. Self-assembly and characterization of supramolecular [60]fullerene-containing 2,6-diacylamidopyridine with uracil derivative by hydrogen-bonding interaction. Org Lett 4 (2002) 1179-1182
22. Xiao S.Q., Li Y.L., Fang H.J., Li H.M., Liu H.B., Shi Z.Q., et al. Synthesis and characterization of three novel [60]fullerene derivatives toward self-assembled nanoparticles through interaction of hydrogen bonding. Org Lett 4 (2002) 3063-3066
23. Liu Y., Xiao S.Q., Li H.M., Li Y.L., Liu H.B., Lu F.S., et al. Self-assembly and characterization of a novel hydrogen-bonded nanostructure. J Phys Chem B 108 (2004) 6256-6260
24. Zhuang J.P., Zhou W.D., Li X.F., Li Y.J., Wang N., He X.R., et al. Multiple hydrogen-bond-induced supramolecular nanostructure from a pincer-like molecule and a [60]fullerene derivative. Tetrahedron 61 (2005) 8686-8693
25. Kaletas B.K., Dobrawa R., Sautter A., Würthner F., Zimine M., De Cola L., et al. Photoinduced electron and energy transfer processes in a bichromophoric pyrene-perylene bisimide system. J Phys Chem A 108 (2004) 1900-1909
26. 60 starting from malonates. J Chem Soc Perkin Trans 1 11 (1997) 1595-1596
27. Richardson C.F., Schuster D.I., and Wilson S.R. Synthesis and characterization of water-soluble amino fullerene derivatives. Org Lett 2 (2000) 1011-1014
28. Bright R., Coote S.J., Freeman S., Hayes D., Smith G., and Tapolczay D. 5-Bromobarbituric acid: a mild and selective monobrominating agent employed in the synthesis of the Gastrin antagonist. Synth Commun 26 (1996) 4195-4206
29. Mosher H.S., and Whitmore F.C. Heterocyclic basic compounds II aminoalkylamino-S-triazines. J Am Chem Soc 67 (1945) 662-664
30. Winnik F.M. Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chem Rev 93 (1993) 587-614
31. Winnik F.M., Tamai N., Yonezawa J., Nishimura Y., and Yamazaki I. Temperature-induced phase transition of pyrene-labeled (hydroxypropyl) cellulose in water: picosecond fluorescence studies. J Phys Chem 96 (1992) 1967-1972
32. Matsui J., Mitsuishi M., and Miyashita T. Characterization of the molecular environment of polymer Langmuir-Blodgett films using a pyrene fluorescent probe. Macromolecules 32 (1999) 381-386
33. Sautter A., Thalacker C., and Würthner F. Hierarchical organization of functional perylene chromophore to esoscopic superstructures by hydrogen bonding and π-π interactions. Adv Mater 11 (1999) 754-758
34. Würthner F., Thalacker C., Sautter A., Schärtl W., Ibach W., and Hollricher O. Hierarchical self-organization of perylene bisimide-melamine assemblies to fluorescent mesoscopic superstructures. Chem Eur J 6 (2000) 3871-3886
35. Arimori S., Bell M.L., Oh C.S., and James T.D. A modular fluorescence intramolecular energy transfer saccharide sensor. Org Lett 4 (2002) 4249-4251
36. 60 in Langmuir-Blodgett films. Chem Phys Lett 280 (1997) 315-320
37. Turro N.J. Modern molecular photochemistry (1978), Benjamin Cummings, Menlo Park (CA)
38. 60 in Langmuir-Blodgett films. Langmuir 14 (1998) 3343-3346
39. Chang S.K., Engen D.V., Fan E., and Hamilton A.D. Hydrogen bonding and molecular recognition: synthetic, complexation and structural studies on barbiturate binding to an artificial receptor. J Am Chem Soc 113 (1991) 7640-7645
40. Tecilla P., Dixon R.P., Slobodkin G., Alavi D.S., Waldeck D.H., and Hamilton A.D. Hydrogen-bonding self-assembly of multichromophore structures. J Am Chem Soc 112 (1990) 9408-9410
41. Binder W.H., Kunz M.J., Kluger C., Hayn G., and Saf R. Synthesis and analysis of telechelic polyisobutylenes for hydrogen-bonded supramolecular pseudo-block copolymers. Macromolecules 37 (2004) 1749-1759
42. Vreekamp R.H., Van Duynhoven J.P.M., Hubert M., Verboom W., and Reinhoudt D.N. Molecular boxes based on calix[4]arene double rosettes. Angew Chem Int Ed 35 (1996) 1215-1218
43. Giovanelli L., and Lay G.L. A chemical and morphological study of fullerene derivatives Langmuir-Blodgett films. Appl Surf Sci 162-163 (2000) 513-518
44. 60 Langmuir-Blodgett films in situ at the air-water interface and ex situ on substrates. Langmuir 16 (2000) 1311-1318
45. Barazzouk S., Hotchandani S., and Kamat P.V. Nanostructured fullerene films. Adv Mater 13 (2001) 1614-1617
46. Li J., Qin D., Baker J.R., and Tomalia D.A. Reversible structure destruction of intramolecular polycomplexes formed by poly(acryamide) and poly(vinyl alcohol), under hydrodynamic shear flow. Macromol Symp 166 (2001) 255-260
47. Das G., Ouali L., Adrian M., Baumeister B., Wilkinson K.J., and Matile S. β-Fibrillogenesis from rigidrod β-barrels: hierarchical preorganization beyond microns. Angew Chem Int Ed 40 (2001) 4657-4661
48. Zhang X.J., Zhang X.H., Shi W.S., Meng X.M., Lee C., and Lee S. Morphology-controllable synthesis of pyrene nanostructures and its morphology dependence of optical properties. J Phys Chem B 109 (2005) 18777-18780