Synergistic Effect of Tetraaryl Porphyrins Containing Corannulene and Other Polycyclic Aromatic Fragments as Hosts for Fullerenes. Impact of C60 in a Statistically Distributed Mixture of Atropisomers.

Symmetric meso-tetraarylporphyrins bearing phenanthrene, pyrene, and corannulene moieties in meta positions have been synthesized in a straightforward procedure under microwave irradiation by quadruple Suzuki-Miyaura reactions. Their (1)H NMR spectra showed the typical pattern of four atropisomers distributed according to their statistical ratio not properly separable due to their fast isomerization. Their ability to bind buckminsterfullerene has been tested with the whole mixture, and different behaviors have been found, α4 isomer corannulene-substituted porphyrins being the best hosts in the family.

[1]  A. Sygula,et al.  Bis-corannulene Receptors for Fullerenes Based on Klärner's Tethers: Reaching the Affinity Limits. , 2015, Organic letters.

[2]  A. Sygula,et al.  A 2:1 receptor/C60 complex as a nanosized universal joint. , 2015, Angewandte Chemie.

[3]  C. Hunter,et al.  Influence of receptor flexibility on intramolecular H-bonding interactions. , 2015, Organic & biomolecular chemistry.

[4]  L. García-Escudero,et al.  Assembling nonplanar polyaromatic units by click chemistry. Study of multicorannulene systems as host for fullerenes. , 2015, Organic letters.

[5]  M. Kawano,et al.  Supramolecular interaction of fullerenes with a curved π-surface of a monomeric quadruply ring-fused porphyrin. , 2015, Chemistry.

[6]  Sílvia Osuna,et al.  Sponge-like molecular cage for purification of fullerenes , 2014, Nature Communications.

[7]  Wei‐chuwan Lin,et al.  Template-directed synthesis of flexible porphyrin nanocage and nanorings via one-step olefin metathesis. , 2014, Journal of the American Chemical Society.

[8]  L. García-Escudero,et al.  Enhanced association for C70 over C60 with a metal complex with corannulene derivate ligands. , 2014, Dalton transactions.

[9]  X. Fang,et al.  Clawlike tripodal porphyrin trimer: ion-controlled on–off fullerene binding. , 2014, The Journal of organic chemistry.

[10]  A. Filoramo,et al.  Supramolecular chemistry of carbon nanotubes. , 2014, Topics in current chemistry.

[11]  M. Stuparu.  Rationally designed polymer hosts of fullerene. , 2013, Angewandte Chemie.

[12]  Michael Kathan,et al.  Corannulenylferrocenes: towards a 1D, non-covalent metal-organic nanowire. , 2012, Chemical communications.

[13]  J. Siegel,et al.  Kilogram-Scale Production of Corannulene , 2012 .

[14]  J. Elguero,et al.  Atropisomerism and conformational aspects of meso-tetraarylporphyrins and related compounds , 2011 .

[15]  C. Hunter,et al.  Dissection of complex molecular recognition interfaces. , 2011, Journal of the American Chemical Society.

[16]  D. Williams,et al.  Drying of organic solvents: quantitative evaluation of the efficiency of several desiccants. , 2010, The Journal of organic chemistry.

[17]  J. FRASER STODDART,et al.  Noncovalent functionalization of single-walled carbon nanotubes. , 2009, Accounts of chemical research.

[18]  M. Neves,et al.  Kinetic study of meso‐tetraphenylporphyrin synthesis under microwave irradiation , 2008 .

[19]  J. A. Paixão,et al.  Microwave-assisted synthesis of porphyrins and metalloporphyrins: a rapid and efficient synthetic method , 2007 .

[20]  Davide Bonifazi,et al.  Supramolecular [60]fullerene chemistry on surfaces. , 2007, Chemical Society reviews.

[21]  N. Miyaura,et al.  Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes. , 2005, Journal of the American Chemical Society.

[22]  H. Wegner,et al.  A new suzuki-heck-type coupling cascade: indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons. , 2003, The Journal of organic chemistry.

[23]  I. Fridovich,et al.  Rotational isomers of N-alkylpyridylporphyrins and their metal complexes. HPLC separation, (1)H NMR and X-ray structural characterization, electrochemistry, and catalysis of O(2)(.-) disproportionation. , 2002, Inorganic chemistry.

[24]  W. Rettig,et al.  Synthesis and Spectroscopic Properties of Arene-Substituted Pyrene Derivatives as Model Compounds for Fluorescent Polarity Probes , 2001 .

[25]  K. A. Srinivas,et al.  MICROWAVE-ASSISTED SYNTHESIS OF 5,10,15,20-TETRAARYL PORPHYRINS , 2001 .

[26]  Allen G. Oliver,et al.  SELECTIVE SUPRAMOLECULAR PORPHYRIN/FULLERENE INTERACTIONS , 1999 .

[27]  C. Reed,et al.  π-Arene/Cation Structure and Bonding. Solvation versus Ligand Binding in Iron(III) Tetraphenylporphyrin Complexes of Benzene, Toluene, p-Xylene, and [60]Fullerene , 1999 .

[28]  K. Maitra,et al.  Interaction of Curved and Flat Molecular Surfaces. The Structures of Crystalline Compounds Composed of Fullerene (C60, C60O, C70, and C120O) and Metal Octaethylporphyrin Units , 1999 .

[29]  B. Meunier,et al.  Illustrating atropisomerism in the porphyrin series using NMR spectroscopy , 1999 .

[30]  B. Desmazières,et al.  Efficient Preparation of the .alpha.,.alpha.,.beta.,.beta.-Atropoisomer of meso-Tetrakis(o-aminophenyl)porphyrin , 1995 .

[31]  M. Crossley,et al.  Steric effects on atropisomerism in tetraarylporphyrins , 1987 .