Abstract
In the past few years, much attention has been devoted to the development of C60 multiadducts for high-added value materials. C60 fullerene can be considered as a versatile hard nanocore for globular systems due to its tuneable valency (1 to 6 based on cyclopropanation derivatization) and regioselective polyaddition. Therefore, hexakisadducts of C60 are becoming an important class of carbon-based macromolecules as they offer wider possibilities for structural variations than any other organic (or inorganic) scaffolds. For example, several types of molecular geometries can be designed and controlled, thanks to regioselective functionalization methodologies. This in turn leads to new building blocks for defined supramolecular organizations. In this review, an overview of the relationships between molecular architecture and self- or induced organization of C60 hexakisadducts is provided. This includes a description of thin films, liquid-crystalline mesophases, and nanospheres formed by such carbonaceous systems.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Guldi DM, Zerbetto F, Georgakilas V, Prato M (2005) Acc Chem Res 38:38
Kraütler B, Maynollo J (1995) Angew Chem Int Ed Engl 34:87
Schwenninger R, Müller T, Kraütler B (1997) J Am Chem Soc 119:9317
Kraütler B, Müller T, Duarte-Ruiz A (2001) Chem Eur J 7:3223
Isaac L, Haldimann RF, Diederich F (1994) Angew Chem Int Ed Engl 33:2339
Isaac L, Seiler P, Diederich F (1995) Angew Chem Int Ed Engl 34:1466
Diederich F, Thilgen C (1996) Science 271:317
Cardullo F, Isaac L, Diederich F, Gisselbrecht JP, Boudon C, Gross M (1996) Chem Comm 797
Isaac L, Diederich F, Haldimann RF (1997) Helv Chim Acta 80:317
Tsukruk VV, Everson MP, Lander LM, Brittain WJ (1996) Langmuir 12:3905
Akiyama T, Imahori H, Ajawakom A, Sakata Y (1996) Chem Lett 907
Dominguez O, Echegoyen L, Cunha F, Tao N (1998) Langmuir 14:821
Kelly KF, Shon YS, Lee TR, Halas N (1999) J Phys Chem B 103:8639
Enger O, Nuesch F, Fibbioli M, Echegoyen L, Preysch E, Diederich F (2000) J Mater Chem 10:2231
Imahori H, Norieda H, Yamada H, Nishimura Y, Yamazaki I, Sakata Y, Fukuzumi S (2001) J Am Chem Soc 123:100
Hirayama D, Takimiya K, Aso Y, Otsubo T, Hasobe T, Yamada H, Imahori H, Fukuzumi S, Sakata Y (2002) J Am Chem Soc 124:532
Hetzer M, Bayerl S, Camps X, Vostrowsky O, Hirsch A, Bayerl TM (1997) Adv Mater 9:913
Nakashima N, Nonaka Y, Nakanishi T, Sagara T, Murakami HJ (1998) Phys Chem B 102:7328
Nakashima N, Tokunaga T, Nakanishi T, Murakami H, Sagara T (1998) Angew Chem Int Ed 37:2671
Hetzer M, Karakatsanis P, Casalta H, Hirsch A, Camps X, Vostrowski O, Bayerl TM (2000) J Phys Chem A 7:1766
Nakashima N, Sakai M, Murakami H, Sagara T, Wakahara T, Akasaka TJ (2002) Phys Chem B 106:3523
Obeng YS, Bard AJ (1991) J Am Chem Soc 113:6279
Bulhoes LOS, Obeng YS, Bard AJ (1993) Chem Mater 5:110
Matsumoto M, Tachibana H, Azumi R, Tanaka M, Nakamura T, Yunome G, Abe M, Yamago S, Nakamura E (1995) Langmuir 11:660
Jonas U, Cardullo F, Belik P, Diederich F, Gügel A, Harth E, Herrmann A, Isaacs L, Müllen K, Ringsdorf H, Thilgen C, Uhlmann P, Vasella A, Waldraff CAA, Walter M (1995) Chem Eur J 1:243
Wang S, Leblanc RM, Arias F, Echegoyen L (1997) Langmuir 13:1672
Guldi DM, Maggini M, Mondini S, Guérin F, Fendler JH (2000) Langmuir 16:1311
Chen K, Caldwell WB, Mirkin CA (1993) J Am Chem Soc 115:1193
Kitajima N, Komatsuzaki H, Hikichi S, Osawa M, Morooka Y (1994) J Am Chem Soc 116:11596
Yamada H, Imahori H, Fukuzumi S (2002) J Mater Chem 12:2034
Wei TX, Zhai J, Ge JH, Gan LB, Huang CH, Luo GB, Ying LM, Liu TT, Zhao XS (1999) Appl Surf Sci 151:153
Hernandez MP, Monroy F, Ortega F, Rubio RG (2001) Langmuir 17:3317
Noworyta K, Kuran P, Nantsis EA, Bilewicz R, Dunsch L, Kutner W (2001) Synth Metals 123:157
Gallani JL, Felder D, Guillon D, Heinrich B, Nierengarten JF (2002) Langmuir 18:2908
Mouri E, Nakanishi T, Nakashima N, Matsuoka H (2002) Langmuir 18:10042
Metzger RM, Baldwin JW, Shumate WJ, Peterson IR, Mani P, Mankey GJ, Morris T, Szulczewski G, Bosi S, Prato M, Comito A, Rubin Y (2003) J Phys Chem B 107:1021
Conoci S, Guldi DM, Nardis S, Paolesse R, Kordatos K, Prato M, Ricciardi G, Vicente MGH, Zilbermann I, Valli L (2004) Chem Eur J 10:6523
Tang Z, Padmawar PA, Canteenwala T, Gao Y, Watkins E, Majewski J, Chiang LY, Wang HL (2006) Langmuir 22:5366
Cardinali F, Gallani JL, Schergna S, Maggini M, Nierengarten JF (2005) Tetrahedron Lett 46:2969
Cardullo F, Diederich F, Echegoyen L, Habicher T, Jayaraman N, Leblanc RM, Fraser Stoddart J, Wang S (1998) Langmuir 14:1955
Hirano C, Imae T, Fujima S, Yanagimoto Y, Takaguchi Y (2005) Langmuir 21:272
Nierengarten JF, Schall C, Nicoud JF, Heinrich B, Guillon D (1998) Tetrahedron Lett 39:5747
Felder D, Gutiérrez Nava M, del Pilar CM, Eckert JF, Luccisano M, Schall C, Masson P, Gallani JL, Heinrich B, Guillon D, Nierengarten JF (2002) Helv Chim Acta 85:288
Felder D, del Pilar CM, Gallani JL, Guillon D, Nierengarten JF, Chuard T, Deschenaux R (2001) Helv Chim Acta 84:1119
Felder D, Gallani JL, Guillon D, Heinrich B, Nicoud JF, Nierengarten JF (2000) Angew Chem Int Ed 39:201
Nierengarten JF, Eckert JF, Rio Y, del Pilar CM, Gallani JL, Guillon D (2001) J Am Chem Soc 123:9743
Zhang S, Rio Y, Cardinali F, Bourgogne C, Gallani JL, Nierengarten JF (2003) J Org Chem 68:9787
Nakamura T, Tachibana H, Yamura M, Matsumoto M, Azumi R, Tanaka M, Kawabata Y (1992) Langmuir 8:4
Wang P, Shamsuzzoha M, Wu SL, Lee WJ, Metzger RM (1992) J Phys Chem 96:9025
Maierhofer AP, Brettreich M, Burghardt S, Vostrowsky O, Hirsch A, Langridge S, Bayerl TM (2000) Langmuir 16:8884
Burghardt S, Hirsch A, Medard N, Kachfhe RA, Aussere D, Valignat MP, Gallani JL (2005) Langmuir 21:7540
Gao Y, Tang Z, Watkins E, Majewski J, Wang HL (2005) Langmuir 21:1416
Felder-Flesch D, Bourgogne C, Gallani JL, Guillon D (2005) Tetrahedron Lett 46:6507
Hartnagel U, Hirsch A, Felder-Flesch D, Gallani JL, Bourgogne C (2008) J Exp Nanosci 3:229
Pauluth D, Geelhaar T (1997) Nachr Chem Tech Lab 45:9
Imahori H, Fukuzumi S (2004) Adv Funct Mater 14:525
Prato M (1999) In: Hirsch A (ed) Fullerenes and related structures. Springer, Heidelberg
Breittreich M, Burghardt S, Böttcher C, Bayerl TM, Bayerl S, Hirsch A (2000) Angew Chem Int Ed 39:1845
Wudl F (2002) J Mater Chem 12:1959
Chuard T, Deschenaux R (2002) J Mater Chem 12:1944
Braun M, Hartnagel U, Ravanelli E, Schade B, Böttcher C, Vostrowsky O, Hirsch A (2004) Eur J Org Chem 1983
Kimura M, Saito K, Ohta K, Hanabusa K, Shirai H, Kobayashi N (2002) J Am Chem Soc 124:5274
Felder D, Heinrich B, Guillon D, Nicoud JF, Nierengarten JF (2000) Chem Eur J 6:3501
Bushby RJ, Hamley IW, Liu Q, Lozman OR, Lydon JE (2005) J Mater Chem 15:4429
Chuard T, Deschenaux R (1996) Helv Chim Acta 79:736
Even M, Heinrich B, Guillon D, Guldi DM, Prato M, Deschenaux R (2001) Chem Eur J 7:2595
Allard E, Oswald F, Donnio B, Guillon D, Delgado JL, Langa F, Deschenaux R (2005) Org Lett 7:383
Campidelli S, Deschenaux R, Eckert J-F, Guillon D, Nierengarten J-F (2002) Chem Commun 656
Campidelli S, Vasquez E, Milic D, Prato M, Barbera J, Guldi DM, Marcaccio M, Paolucci D, Paolucci F, Deschenaux R (2004) J Mater Chem 14:1266
Campidelli S, Lenoble J, Barbera J, Paolucci F, Marcaccio M, Paolucci D, Deschenaux R (2005) Macromolecules 38:7915
Lenoble J, Maringa N, Campidelli S, Donnio B, Guillon D, Deschenaux R (2006) Org Lett 8:1851
Deschenaux R, Even M, Guillon D (1998) Chem Commun 5:537
Hetzer M, Gutberlet T, Brown MF, Camps X, Vostrowsky O, Schönberger H, Hirsch A, Bayerl TM (1999) J Phys Chem A 103:637
Dardel B, Deschenaux R, Even M, Serrano E (1999) Macromolecules 32:5193
Dardel B, Guillon D, Heinrich B, Deschenaux R (2001) J Mater Chem 11:2814
Campidelli S, Deschenaux R (2001) Helv Chim Acta 84:589
Guillon D, Nierengarten JF, Gallani JL, Eckert JF, Rio Y, del Pilar CM, Dardel R, Deschenaux R (2003) Macromol Symp 192:63
Tirelli N, Cardullo F, Habicher T, Suter UW, Diederich F (2000) J Chem Soc Perkin Trans 2:193
Campidelli S, Eng C, Saez IM, Goodby JW, Deschenaux R (2003) Chem Commun 1520
Felder-Flesch D, Rupnicki L, Bourgogne C, Donnio B, Guillon D (2006) J Mater Chem 16:304
Chuard T, Deschenaux R, Hirsch A, Schönberger H (1999) Chem Commun 2103
Sawamura M, Kawai K, Matsuo Y, Kanie K, Kato T, Nakamura E (2002) Nature 419:702
Nakamura E, Isobe H (2003) Acc Chem Res 36:807
Matsuo Y, Muramatsu A, Hamasaki R, Mizoshita N, Kato T, Nakamura E (2004) J Am Chem Soc 126:432
Gottis S, Kopp C, Allard E, Deschenaux R (2007) Helv Chim Acta 90:957
Merkel K, Kocot A, Mehl GH, Meyer T (2004) J Chem Phys 121:5012
Frigoli M, Mehl GH (2004) Eur J Org Chem 3:636
Tajber L, Kocot A, Vij JK, Merkel K, Kalewska-Rejdak J, Mehl GH, Elsasser R, Goodby JW, Veith M (2002) Macromolecules 35:8601
Alvarez R, Mehl GH (2005) Mol Cryst Liq Cryst 439:2125
Merkel K, Kocot A, Vij JK, Korlacki R, Mehl GH, Meyer T (2004) Phys Rev Lett 93:237801
Frigoli M, Mehl GH (2004) Chem Commun 2040
Shepperson KJ, Meyer T, Mehl GH (2004) Mol Cryst Liq Cryst 41:1227
Mehl GH, Goodby JW (1996) Angew Chem Int Ed Engl 35:2641
Goodby JW, Mehl GH, Saez IM, Tuffin RP, Mackenzie G, Auzély-Velty R, Benvegnu T, Plusquellec D (1998) Chem Commun 2057
Mehl GH, Saez IM (1999) Appl Organomet Chem 13:261
Saez IM, Goodby JW (2001) J Mater Chem 11:2845
Saez IM, Goodby JW, Richardson RM (2001) Chem Eur J 7:2758
Saez IM, Goodby JW (2005) J Mater Chem 15:26
Cseh L, Mehl GH (2006) J Am Chem Soc 128:13376
Qi H, Hegmann TJ (2006) Mater Chem 16:4197
Hegmann T, Qi H, Marx VM (2007) J Inorg Organomet Polym Mater 17:483
Marx VM, Girgis H, Heiney PA, Hegmann TJ (2008) Mater Chem 18:2983
Qi H, Hegmann T (2008) Adv Funct Mater 18:212
Qi H, Kinkead B, Marx VN, Zhang HR, Hegmann T (2009) Chem Phys Chem 10:1211
Frein S, Boudon J, Vonlanthen M, Scharf T, Barbera J, Süss-Fink G, Bürgi T, Deschenaux R (2008) Helv Chim Acta 91:2321
Donnio B, García-Vázquez P, Gallani JL, Guillon D, Terazzi E (2007) Adv Mater 19:3534
Zeng X, Liu F, Fowler AG, Ungar G, Cseh L, Mehl GH, Macdonald JE (2009) Adv Mater 21:1746
Demortière A, Buathong S, Pichon B, Panissod P, Guillon D, Bégin-Colin S, Donnio B (2010) Small 6:1341
Donnio B, Derory A, Terazzi E, Drillon M, Guillon D, Gallani JL (2010) Soft Matter 6:965
Campidelli S, Brandmüller T, Hirsch A, Saez IM, Goodby JW, Deschenaux R (2006) Chem Commun 4282
Mamlouk H, Heinrich B, Bourgogne C, Donnio B, Guillon D, Felder-Flesch D (2007) J Mater Chem 17:2199
Freeman AI, Mayhew E (1986) Cancer 58:573
Seltzer SE (1989) Radiology 171:19
Lasic DD, Papahadjopoulos D (1995) Science 267:1275
Tien HT, Salamon Z, Ottova A (1991) Crit Rev Biomed Eng 18:323
Ferrari M (2005) Nat Rev Cancer 5:161
Litman BJ (1973) Biochemistry 12:2545
Nishiyama N, Kataoka K (2006) Pharmacol Ther 112:630
Fu K, Kitaygorodskiy A, Sun YP (2000) Chem Mater 12:2073
Hetzer M, Clausen-Schaumann H, Bayerl S, Bayerl TM, Camps X, Vostrowsky O, Hirsch A (1999) Angew Chem Int Ed 38:1962
Hetzer M, Bayerl S, Bayerl TM, Camps X, Vostrowsky O, Hirsch A (1997) In: Kuzmany H, Fink J, Mehring M, Roth S (eds) Molecular nanostructures. World Scientific, New York, USA
Burghardt S, Hirsch A, Schade B, Ludwig K, Böttcher C (2005) Angew Chem Int Ed Engl 44:2976
Partha R, Lacjey M, Hirsch A, Ward Casscells S, Conyers JL (2007) J Nanobiotech 5:6
Schade B, Ludwig K, Böttcher C, Hartnagel U, Hirsch A (2007) Angew Chem Int Ed 46:4393
Terazzi E, Bourgogne C, Welter R, Gallani JL, Guillon D, Rogez G, Donnio B (2008) Angew Chem Int Ed 47:490
Acknowledgments
I would like to thank, in particular, Drs. J.-L. Gallani and B. Donnio for many discussions. I would also like to thank my research colleagues, Drs. B. Heinrich, C. Bourgogne, D. Guillon for their collaboration, and N. Beyer, E. Couzigné and E. Voirin for their technical assistance.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Felder-Flesch, D. (2013). Self- or Induced Organization of [60]Fullerene Hexakisadducts. In: Nierengarten, JF. (eds) Fullerenes and Other Carbon-Rich Nanostructures. Structure and Bonding, vol 159. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2013_111
Download citation
DOI: https://doi.org/10.1007/430_2013_111
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-54853-6
Online ISBN: 978-3-642-54854-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)