Selective synthesis of [7]- and [8]cycloparaphenylenes.

Cycloparaphenylenes (CPPs) are a remarkable class of hoop-shaped conjugated macrocycles with inimitable properties. Herein we describe a divergent synthesis of [7]CPP and [8]CPP. Furthermore we present the first crystal structure of [7]CPP. Thus, we have now established the size-selective synthesis of [n]CPP (n = 7-16) in a uniformed cyclohexane-based method.

[1]  K. Itami,et al.  Initiation of carbon nanotube growth by well-defined carbon nanorings. , 2013, Nature chemistry.

[2]  Toshiyasu Suzuki,et al.  Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes , 2013 .

[3]  Y. Kanemitsu,et al.  Excited States in Cycloparaphenylenes: Dependence of Optical Properties on Ring Length. , 2012, The journal of physical chemistry letters.

[4]  R. Jasti,et al.  Gram-scale synthesis and crystal structures of [8]- and [10]CPP, and the solid-state structure of C60@[10]CPP , 2012 .

[5]  S. Irle,et al.  Combined experimental and theoretical studies on the photophysical properties of cycloparaphenylenes. , 2012, Organic & biomolecular chemistry.

[6]  E. Darzi,et al.  Selective syntheses of [7]-[12]cycloparaphenylenes using orthogonal Suzuki-Miyaura cross-coupling reactions. , 2012, The Journal of organic chemistry.

[7]  Toshiyasu Suzuki,et al.  Selective synthesis and crystal structure of [10]cycloparaphenylene. , 2012, Organic letters.

[8]  H. Shinohara,et al.  Size-selective synthesis of [9]–[11] and [13]cycloparaphenylenes , 2012 .

[9]  K. Itami,et al.  Synthesis of cycloparaphenylenes and related carbon nanorings: a step toward the controlled synthesis of carbon nanotubes. , 2012, Accounts of chemical research.

[10]  K. Itami.  Toward controlled synthesis of carbon nanotubes and graphenes , 2012 .

[11]  R. Jasti,et al.  Synthesis, characterization, and crystal structure of [6]cycloparaphenylene. , 2012, Angewandte Chemie.

[12]  M. Iyoda,et al.  Conjugated macrocycles: concepts and applications. , 2011, Angewandte Chemie.

[13]  Matthew R. Golder,et al.  Selective synthesis of strained [7]cycloparaphenylene: an orange-emitting fluorophore. , 2011, Journal of the American Chemical Society.

[14]  S. Yamago,et al.  Size-selective encapsulation of C60 by [10]cycloparaphenylene: formation of the shortest fullerene-peapod. , 2011, Angewandte Chemie.

[15]  Toshiyasu Suzuki,et al.  Selective and random syntheses of [n]cycloparaphenylenes (n=8-13) and size dependence of their electronic properties. , 2011, Journal of the American Chemical Society.

[16]  K. Itami,et al.  [9]Cycloparaphenylene : Nickel-mediated Synthesis and Crystal Structure , 2011 .

[17]  N. Tokitoh,et al.  Concise synthesis and crystal structure of [12]cycloparaphenylene. , 2011, Angewandte Chemie.

[18]  K. Itami,et al.  A modular and size-selective synthesis of [n]cycloparaphenylenes: a step toward the selective synthesis of [n,n] single-walled carbon nanotubes. , 2010, Angewandte Chemie.

[19]  S. Bachrach,et al.  DFT study of cycloparaphenylenes and heteroatom-substituted nanohoops. , 2010, The Journal of organic chemistry.

[20]  D. Sundholm,et al.  Magnetically induced currents in [n]cycloparaphenylenes, n = 6-11. , 2010, The Journal of organic chemistry.

[21]  K. Itami,et al.  Theoretical studies on the structures and strain energies of cycloparaphenylenes. , 2010, Organic letters.

[22]  Fabio Pichierri,et al.  Calculation of absorption and emission spectra of [n]cycloparaphenylenes: the reason for the large Stokes shift. , 2010, Physical chemistry chemical physics : PCCP.

[23]  S. Yamago,et al.  Synthesis of [8]cycloparaphenylene from a square-shaped tetranuclear platinum complex. , 2010, Angewandte Chemie.

[24]  Yosuke Yamamoto,et al.  Selective synthesis of [12]cycloparaphenylene. , 2009, Angewandte Chemie.

[25]  L. T. Scott,et al.  New strategies for synthesizing short sections of carbon nanotubes. , 2009, Angewandte Chemie.

[26]  C. Bertozzi,et al.  Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures , 2008, Journal of the American Chemical Society.

[27]  Rudolf J. Vermeij,et al.  Nonplanar aromatic compounds. Part 10: A strategy for the synthesis of aromatic belts-all wrapped up or down the tubes? , 2008 .

[28]  Takeshi Kawase,et al.  Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities: exploration of the concave-convex pi-pi interaction. , 2006, Chemical reviews.

[29]  Y. Tobe,et al.  Molecular loops and belts. , 2006, Chemical reviews.

[30]  L. T. Scott,et al.  Conjugated belts and nanorings with radially oriented p orbitals. , 2003, Angewandte Chemie.

[31]  J. Chandrasekhar,et al.  The Interplay of Angle Strain and Aromaticity: Molecular and Electronic Structures of [0n]Paracyclophanes , 2000 .

[32]  F. Vögtle,et al.  Auf dem Weg zu makrocyclischen para-Phenylenen , 1993 .

[33]  S. Irle,et al.  Origin of the size-dependent fluorescence blueshift in [n]cycloparaphenylenes , 2013 .