SYNTHESIS OF A FULLERENE[60] CRYPTATE AND SYSTEMATIC LANGMUIR-BLODGETT AND THIN-FILM INVESTIGATIONS OF AMPHIPHILIC FULLERENE DERIVATIVES

The synthesis of the first fullerene cryptate 7 with a sodium ion bound to a benzo[2.2.2]cryptand covalently attached to a methanofullerene[60] is described. The amphiphilic properties of 7 as well as of a variety of other covalent fullerene derivatives with polar functional groups and the ability of these compounds to form Langmuir monolayers at the air-water interface were investigated in a systematic study. Among these derivatives are Diels-Alder adducts of C60 and methanofullerenes, four of which are fullerene C-glycosides. The films at the water surface were characterized by their surface pressure versus molecular area isotherms, compression and expansion cycles, and optical light microscopy. UV/Vis spectroscopy and small-angle X-ray diffraction (SAXS) were employed for LB film characterization on solid substrates. Parameters influencing the spreading and monolayer character include (a) polarity, (b) balance of hydrophobicity to hydrophilicity, (c) size and bulkiness of the polar groups attached to the fullerene, and (d) presence of aromatic residues in these groups.

[1]  E. Harth,et al.  Glycosylidene Carbenes. Part 20. Synthesis of deprotected, spiro‐linked C‐glycosides of C60 , 1994 .

[2]  F. Diederich,et al.  Tether-Directed Remote Functionalization of Buckminsterfullerene: Regiospecific Hexaadduct Formation† , 1994 .

[3]  W. B. Caldwell,et al.  A WELL-DEFINED SURFACE-CONFINABLE FULLERENE : MONOLAYER SELF-ASSEMBLY ON AU(111) , 1994 .

[4]  François Diederich,et al.  Spacer‐kontrollierte Fernfunktionalisierung von Buckminsterfulleren: regiospezifische Bildung eines Hexaadduktes , 1994 .

[5]  Z. Yao,et al.  Langmuir-Blodgett film of C60/TTF derivatives , 1994 .

[6]  J. Atwood,et al.  Ball and Socket Nanostructures: New Supramolecular Chemistry Based on Cyclotriveratrylene , 1994 .

[7]  M. Prato,et al.  Incorporation of an Acyl Group in Fulleropyrrolidines: Effects on Langmuir Monolayers , 1994 .

[8]  Aiqin Wang,et al.  Langmuir-Blodgett film of 1,3,6,11,13,18,28,31-octabromofullerene-C60 , 1994 .

[9]  Yves Rubin,et al.  Photophysical Characterization and Singlet Oxygen Yield of a Dihydrofullerene , 1994 .

[10]  M. Prato,et al.  Electrochemically Induced Isomerization of a Fulleroid to a Methanofullerene , 1994 .

[11]  Jie Zheng,et al.  Non-linear coupling of a C60-Langmuir-Blodgett-film-coated waveguide , 1994 .

[12]  R. Henderson,et al.  Influence of the AlAs mode fraction on the luminescence efficiency of ?As quantum well structures , 1994 .

[13]  C. Hawker,et al.  The Synthesis and Characterization of a Self-Assembling Amphiphilic Fullerene , 1994 .

[14]  P. Siciliano,et al.  Optical properties of Langmuir-Blodgett films of the mixture C60-arachidic acid , 1994 .

[15]  Z. Yao,et al.  High-resolution electron microscopy and electron diffraction study on the C[sub 60] Langmuir-Blodgett films , 1994 .

[16]  M. Prato,et al.  Synthesis of N-acylated fulleropyrrolidines: New materials for the preparation of Langmuir-Blodgett films containing fullerenes , 1994 .

[17]  R. A. Uphaus,et al.  Fullerene films and fullerene—dodecylamine adduct monolayers at air—water interfaces studied by neutron and X-ray reflection , 1994 .

[18]  Daoben Zhu,et al.  Formation and structural characteristic of Langmuir-Blodgett films of C60 and C70 , 1994 .

[19]  G. Zou,et al.  A new complex polymeric Langmuir‐Blodgett film of fullerene , 1994 .

[20]  W. Brittain,et al.  Atomic force microscopy of C60 tethered to a self-assembled monolayer , 1994 .

[21]  L. Chernozatonskii,et al.  Two states of C60 film at the air/water interface , 1994 .

[22]  Y. Maruyama,et al.  Redox properties of organofullerenes , 1994 .

[23]  T. Ebbesen,et al.  Crystal Structure, Bonding, and Phase Transition of the Superconducting Na2CsC60 Fulleride , 1994, Science.

[24]  Daoben Zhu,et al.  High resolution electron microscopy study on the structure of C70 Langmuir-blodgett film , 1994 .

[25]  B. Stewart,et al.  Formation and structure of Langmuir–Blodgett films of C60 and arachidic acid , 1994 .

[26]  F. Diederich,et al.  Syntheses, structures, and properties of methanofullerenes , 1994 .

[27]  Roger Taylor,et al.  The chemistry of fullerenes , 1995, Nature.

[28]  Basil I. Swanson,et al.  Surface acoustic wave thin-film chemical microsensors based on covalently bound C60 derivatives: a molecular self-assembly approach , 1993 .

[29]  F. Diederich,et al.  Structures and Chemistry of Methanofullerenes: A Versatile Route into N-[(Methanofullerene)carbonyl]-Substituted Amino Acids , 1993 .

[30]  F. Diederich,et al.  Synthesis of a Fullerene Derivative of Benzo[18]crown‐6 by Diels‐Alder Reaction: Complexation Ability, Amphiphilic Properties, and X‐Ray Crystal Structure of a Dimethoxy‐1,9‐(methano[1,2]benzenomethano)fullerene[60] Benzene Clathrate , 1993 .

[31]  K. Müllen,et al.  THE DIELS-ALDER ADDUCT OF C-60 AND 4,5-DIMETHOXY-O-QUINODIMETHANE SYNTHESIS, CRYSTAL-STRUCTURE, AND DONOR-ACCEPTOR BEHAVIOR , 1993 .

[32]  T. Guarr,et al.  Electrochemistry of the C60H2 fullerene , 1993 .

[33]  Eiichi Nakamura,et al.  Photoinduced biochemical activity of fullerene carboxylic acid , 1993 .

[34]  A. Hirsch.  The Chemistry of the Fullerenes: An Overview , 1993 .

[35]  A. Hirsch.  Die Chemie der Fullerene: ein Überblick , 1993 .

[36]  Chad A. Mirkin,et al.  Self-Assembled Monolayer Films of C60 on Cysteamine-Modified Gold , 1993 .

[37]  M. Petty,et al.  Langmuir-Blodgett films of 1-t-butyl-9-hydrofullerene-60 , 1993 .

[38]  Fred Wudl,et al.  Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification , 1993 .

[39]  R. Strongin,et al.  Langmuir films of fullerene C60, fullerene epoxide C60O, and dihydrofulleroid C61H2 , 1993 .

[40]  F. Diederich,et al.  Improved purification of C60 and formation of σ- and π-homoaromatic methano-bridged fullerenes by reaction with alkyl diazoacetates , 1993 .

[41]  L. J. Peticolas,et al.  A monolayer of C60 tethered to the surface of an inorganic substrate : assembly and structure , 1993 .

[42]  Chad A. Mirkin,et al.  Fullerene self-assembly onto (MeO)3Si(CH2)3NH2-modified oxide surfaces , 1993 .

[43]  K. Müllen,et al.  Reaction of Buckminsterfullerene with ortho‐Quinodimethane: a New Access to Stable C60 Derivatives , 1993 .

[44]  Klaus Müllen,et al.  Umsetzung von Buckminsterfulleren C60 mit ortho-Chinodimethan: ein neuer Zugang zu stabilen C60-Derivaten† , 1993 .

[45]  Y. Obeng,et al.  Langmuir-Blodgett and electrochemical studies of fullerene films , 1993 .

[46]  F. Diederich,et al.  C60 and C70 in a Basket? – Investigations of Mono‐ and Multilayers from Azacrown Compounds and Fullerenes , 1992 .

[47]  F. Wudl,et al.  A polyester and polyurethane of diphenyl C61: retention of fulleroid properties in a polymer , 1992 .

[48]  Y. Achiba,et al.  Morphological study of thin-film systems of pure fullerene (C60) and some other amphiphilic compounds on the electron microscopic scale , 1992 .

[49]  H. Ringsdorf,et al.  C60 and C70 im Körbchen? — Untersuchungen an Mono‐ und Multischichten aus Azakronenverbindungen und Fullerenen , 1992 .

[50]  F. Diederich,et al.  Fullerene Sugars: Preparation of Enantiomerically Pure, Spiro‐Linked C‐Glycosides of C60 , 1992 .

[51]  Wan-Jin Lee,et al.  Order and disorder in fullerene (C60) Langmuir-Blodgett films: direct imaging by scanning tunneling microscopy and high-resolution transmission electron microscopy , 1992 .

[52]  Andrea Vasella,et al.  Fullerenzucker: Herstellung enantiomerenreiner, spiroverknüpfter C-Glycoside von C60† , 1992 .

[53]  R. Lennox,et al.  C{sub 60} and C{sub 70} at the air-water interface , 1992 .

[54]  B. Parkinson,et al.  Electrochemical studies on metal derivatives of buckminsterfullerene (C60) , 1992 .

[55]  Alfredo Pasquarello,et al.  Ring Currents in Icosahedral C60 , 1992, Science.

[56]  Hsien‐Hau Wang,et al.  Discrete layers of ordered fullerene C60 molecules in the cocrystal C60.cntdot.CH2I2.cntdot.C6H6: synthesis, crystal structure, and carbon-13 NMR properties , 1992 .

[57]  F. Wudl,et al.  Synthesis of m-phenylene- and p-phenylenebis(phenylfulleroids): two-pearl sections of pearl necklace polymers , 1992 .

[58]  Daoben Zhu,et al.  Direct observation of C60 LB film with scanning tunneling microscopy , 1992 .

[59]  D. Swenson,et al.  Synthesis and structure of N1-e-benzo-4,7,13,16,21,26-hexaoxa-1,10-diazabicyclo[8.8.8]hexacos-23-yl-N2-phenylthiourea. Derivative of a bifunctional complexing agent , 1992 .

[60]  V. Catalano,et al.  Supramolecular aggregation of an (.eta.2-C60) iridium complex involving phenyl chelation of the fullerene , 1992 .

[61]  Y. Obeng,et al.  Electrochemistry and Langmuir Trough Studies of C60 and C70 Films , 1992 .

[62]  C. Pearson,et al.  Langmuir-Blodgett films of C60 , 1992 .

[63]  Sydney Leach,et al.  Electronic spectra and transitions of the fullerene C60 , 1992 .

[64]  R. Haddon,et al.  Microwave study of superconductivity in alkali-metal-doped fullerene C60 films , 1992 .

[65]  Robert C. Haddon,et al.  Electronic structure, conductivity and superconductivity of alkali metal doped (C60) , 1992 .

[66]  Dawn D. Dominguez,et al.  Incorporation of buckminsterfullerene (C60) in Langmuir-Blodgett films , 1992 .

[67]  Lee W. Tutt,et al.  Optical limiting performance of C60 and C70 solutions , 1992, Nature.

[68]  T. Ebbesen,et al.  Isotope effect on superconductivity in Rb3C60 , 1992, Nature.

[69]  M. Yumura,et al.  Formation of Langmuir-Blodgett films of a fullerene , 1992 .

[70]  F. Wudl,et al.  Systematic Inflation of Buckminsterfillerene C60: Synthesis of Diphenyl Fulleroids C61 to C66 , 1991, Science.

[71]  R. Baughman,et al.  Superconductivity at 45 K in Rb/Tl Codoped C60 and C60/C70 Mixtures , 1991, Science.

[72]  O. Ermer.  3:1 Molecular Complex of Hydroquinone and C60 , 1991 .

[73]  Y. Obeng,et al.  Langmuir films of C60 at the air-water interface , 1991 .

[74]  Smith,et al.  Orientational ordering transition in solid C60. , 1991, Physical review letters.

[75]  R. Kaner,et al.  Alkali-Fulleride Superconductors: Synthesis, Composition, and Diamagnetic Shielding , 1991, Science.

[76]  A. J. Muller,et al.  Conducting films of C60 and C70 by alkali-metal doping , 1991, Nature.

[77]  Y. Rubin,et al.  Characterization of the soluble all-carbon molecules C60 and C70 , 1990 .

[78]  W. Krätschmer,et al.  Solid C60: a new form of carbon , 1990, Nature.

[79]  O. Gansow,et al.  Synthesis and characterization of some bifunctional 2b:2:1 cryptands , 1981 .

[80]  A. I. Popov,et al.  Recovery process for cyptands from nonaqueous solutions of their complexes , 1977 .

[81]  D. Foose,et al.  The crystal structure of cesium hydrogen selenate CsHSeO4(VI) , 1977 .

[82]  Jean-Marie Lehn,et al.  Design of organic complexing agents Strategies towards properties , 1973 .