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Pure Appl. Chem., 1999, Vol. 71, No. 2, pp. 209-219

http://dx.doi.org/10.1351/pac199971020209

Geodesic polyarenes with exposed concave surfaces

L. T. Scott, H. E. Bronstein, D. V. Preda, R. B. M. Ansems, M. S. Bratcher and Stefan Hagen

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  • Chen Min-Kuan, Hsin Hsin-Ju, Wu Tsun-Cheng, Kang Bo-Yan, Lee Yen-Wei, Kuo Ming-Yu, Wu Yao-Ting: Highly Curved Bowl-Shaped Fragments of Fullerenes: Synthesis, Structural Analysis, and Physical Properties. Chem. Eur. J. 2014, 20, 598. <http://dx.doi.org/10.1002/chem.201303357>
  • Zabula Alexander V., Filatov Alexander S., Xia Jianlong, Jasti Ramesh, Petrukhina Marina A.: Tightening of the Nanobelt upon Multielectron Reduction. Angew. Chem. 2013, 125, 5137. <http://dx.doi.org/10.1002/ange.201301226>
  • Zabula Alexander V., Filatov Alexander S., Xia Jianlong, Jasti Ramesh, Petrukhina Marina A.: Tightening of the Nanobelt upon Multielectron Reduction. Angew. Chem. Int. Ed. 2013, 52, 5033. <http://dx.doi.org/10.1002/anie.201301226>
  • Inada Yuhi, Amaya Toru, Shimizu Yasutomo, Saeki Akinori, Otsuka Takeo, Tsuji Ryotaro, Seki Shu, Hirao Toshikazu: Nitrogen-doped Graphitic Carbon Synthesized by Laser Annealing of Sumanenemonoone Imine as a Bowl-shaped π-Conjugated Molecule. Chem. Asian J. 2013, 8, 2569. <http://dx.doi.org/10.1002/asia.201300500>
  • Murray Jane S., Shields Zenaida Peralta-Inga, Lane Pat, Macaveiu Laura, Bulat Felipe A.: The average local ionization energy as a tool for identifying reactive sites on defect-containing model graphene systems. J Mol Model 2013, 19, 2825. <http://dx.doi.org/10.1007/s00894-012-1693-8>
  • Yamada Michio, Akasaka Takeshi, Nagase Shigeru: Carbene Additions to Fullerenes. Chem. Rev. 2013, 113, 7209. <http://dx.doi.org/10.1021/cr3004955>
  • Kawasumi Katsuaki, Zhang Qianyan, Segawa Yasutomo, Scott Lawrence T., Itami Kenichiro: A grossly warped nanographene and the consequences of multiple odd-membered-ring defects. Nature Chem 2013, 5, 739. <http://dx.doi.org/10.1038/nchem.1704>
  • Luzanov A. V.: π-system in a strong electric field. Analysis of electron unpairing. J Struct Chem 2013, 54, 835. <http://dx.doi.org/10.1134/S0022476613050016>
  • Bunz Uwe H. F., Menning Sebastian, Martín Nazario: para-Verknüpfte Cyclophenylene und halbkugelförmige Polyarene: Bausteine für einwandige Kohlenstoffnanoröhren?. Angew. Chem. 2012, 124, 7202. <http://dx.doi.org/10.1002/ange.201201494>
  • Bunz Uwe H. F., Menning Sebastian, Martín Nazario: para-Connected Cyclophenylenes and Hemispherical Polyarenes: Building Blocks for Single-Walled Carbon Nanotubes?. Angew. Chem. Int. Ed. 2012, 51, 7094. <http://dx.doi.org/10.1002/anie.201201494>
  • Zabula Alexander V., Sumner Natalie J., Filatov Alexander S., Spisak Sarah N., Grigoryants Vladimir M., Petrukhina Marina A.: Reshaping Rubrene by Controlled Reduction with Alkali Metals. Eur. J. Inorg. Chem. 2012, 2012, 4675. <http://dx.doi.org/10.1002/ejic.201200164>
  • Dubceac Cristina, Zabula Alexander V., Filatov Alexander S., Rossi Fulvio, Zanello Piero, Petrukhina Marina A.: Bowl-shaped carbocations: easy to produce, hard to reduce. J. Phys. Org. Chem. 2012, 25, 553. <http://dx.doi.org/10.1002/poc.2900>
  • Zabula Alexander V., Spisak Sarah N., Filatov Alexander S., Petrukhina Marina A.: Self-Assembly of Charged Supramolecular Sandwiches Formed by Corannulene Tetraanions and Lithium Cations. Organometallics 2012, 31, 5541. <http://dx.doi.org/10.1021/om300507z>
  • García-Novo Patxi, Campo-Cacharrón Alba, Cabaleiro-Lago Enrique M., Rodríguez-Otero Jesús: Interaction between anions and substituted molecular bowls. PCCP 2012, 14, 104. <http://dx.doi.org/10.1039/c1cp22823d>
  • Rogachev Andrey Yu., Filatov Alexander S., Zabula Alexander V., Petrukhina Marina A.: Functionalized corannulene cations: a detailed theoretical survey. PCCP 2012, 14, 3554. <http://dx.doi.org/10.1039/c2cp23442d>
  • Amaya Toru, Hirao Toshikazu: Bowl-to-bowl inversion of sumanene derivatives. PureAppl Chem 2012, 1. <http://dx.doi.org/10.1351/PAC-CON-11-09-09>
  • Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure-Eight-Strukturen, Möbius-Bänder und mehr: Konformation und Aromatizität von Porphyrinoiden. Angew. Chem. 2011, 123, 4376. <http://dx.doi.org/10.1002/ange.201003353>
  • Zabula Alexander V., Spisak Sarah N., Filatov Alexander S., Rogachev Andrey Yu., Petrukhina Marina A.: A Strain-Releasing Trap for Highly Reactive Electrophiles: Structural Characterization of Bowl-Shaped Arenium Carbocations. Angew Chem 2011, 123, 3027. <http://dx.doi.org/10.1002/ange.201007762>
  • Stępień Marcin, Sprutta Natasza, Latos-Grażyński Lechosław: Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids. Angew. Chem. Int. Ed. 2011, 50, 4288. <http://dx.doi.org/10.1002/anie.201003353>
  • Zabula Alexander V., Spisak Sarah N., Filatov Alexander S., Rogachev Andrey Yu., Petrukhina Marina A.: A Strain-Releasing Trap for Highly Reactive Electrophiles: Structural Characterization of Bowl-Shaped Arenium Carbocations. Angew Chem Int Ed 2011, 50, 2971. <http://dx.doi.org/10.1002/anie.201007762>
  • Wudl Fred, Mohebbi Ali Reza: Electron-Accepting Dithiarubicene (Emeraldicene) and Derivatives Prepared by Unprecedented Nucleophilic Hydrogen Substitution by Alkyllithium Reagents. Chem Eur J 2011, 17, 2642. <http://dx.doi.org/10.1002/chem.201002608>
  • Wang Tao, Tang Fu Ming, Wu Yi Fang: A combined EPR and DFT study of the overcrowded aromatic radical cations from Friedel–Crafts alkylation reactions. J Mol Structure 2011, 1002, 128. <http://dx.doi.org/10.1016/j.molstruc.2011.07.009>
  • Tokimizu Yusuke, Ohta Yusuke, Chiba Hiroaki, Oishi Shinya, Fujii Nobutaka, Ohno Hiroaki: Direct synthesis of highly fused perimidines by copper(I)-catalyzed hydroamination of 2-ethynylbenzaldehydes. Tetrahedron 2011, 67, 5168. <http://dx.doi.org/10.1016/j.tet.2011.05.051>
  • Zabula Alexander V., Dubceac Cristina, Filatov Alexander S., Petrukhina Marina A.: Selective Surface Decoration of Corannulene. J Org Chern 2011, 76, 9572. <http://dx.doi.org/10.1021/jo201765j>
  • Green Jason R., Dunbar Robert C.: When Do Molecular Bowls Encapsulate Metal Cations?. J Phys Chem A 2011, 115, 4968. <http://dx.doi.org/10.1021/jp111843r>
  • Amaya Toru, Hirao Toshikazu: A molecular bowl sumanene. Chem Commn 2011, 47, 10524. <http://dx.doi.org/10.1039/c1cc12532j>
  • Scott Lawrence T., Bronstein Hindy E., Preda Dorin V., Ansems Ronald B. M., Bratcher Matthew S., Hagen Stefan: ChemInform Abstract: Geodesic Polyarenes with Exposed Concave Surfaces. ChemInform 2010, 31, no. <http://dx.doi.org/10.1002/chin.200002272>
  • Filatov Alexander S., Petrukhina Marina A.: Probing the binding sites and coordination limits of buckybowls in a solvent-free environment: Experimental and theoretical assessment. Coord Chem Rev - 2010, 254, 2234. <http://dx.doi.org/10.1016/j.ccr.2010.05.004>
  • Yao Hiroshi, Kurokami Motoi, Kimura Keisaku: Carbon graphite surfaces modified with two-dimensional arrays of N-acetyltripeptide-protected gold nanoparticles. Colloid Surf A Phys Eng Aspects 2010, 361, 174. <http://dx.doi.org/10.1016/j.colsurfa.2010.03.033>
  • Domin Marek A., Steinberg Brian D., Quimby Jennifer M., Smith Natalie J., Greene Allison K., Scott Lawrence T.: Routine analysis and characterization of highly insoluble polycyclic aromatic compounds by direct analysis in real time mass spectrometry (DART). Analyst 2010, 135, 700. <http://dx.doi.org/10.1039/b923300h>
  • Lawrence T. Scott. Angew Chem 2009, 121, 8552. <http://dx.doi.org/10.1002/ange.200904777>
  • Lawrence T. Scott. Angew Chem Int Ed 2009, 48, 8402. <http://dx.doi.org/10.1002/anie.200904777>
  • Steinberg Brian D., Jackson Edward A., Filatov Alexander S., Wakamiya Atsushi, Petrukhina Marina A., Scott Lawrence T.: Aromatic π-Systems More Curved Than C60. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations. J Am Chem Soc 2009, 131, 10537. <http://dx.doi.org/10.1021/ja9031852>
  • dos Santos S G, Pires M S, Lemos V, Freire V N, Caetano E W S, Galvão D S, Sato F, Albuquerque E L: C60-derived nanobaskets: stability, vibrational signatures, and molecular trapping. J of Inst Physics Nanotechnology 2009, 20, 395701. <http://dx.doi.org/10.1088/0957-4484/20/39/395701>
  • Higashibayashi Shuhei: Synthesis of Bowl-shaped Aromatic Hydrocarbons, Buckybowl. J Syn Org Chem Jpn 2009, 67, 38. <http://dx.doi.org/10.5059/yukigoseikyokaishi.67.38>
  • Rodríguez-Morgade M. Salomé, Claessens Christian G., Medina Anaïs, González-Rodríguez David, Gutiérrez-Puebla Enrique, Monge Angeles, Alkorta Ibon, Elguero José, Torres Tomás: Synthesis, Characterization, Molecular Structure and Theoretical Studies of Axially Fluoro-Substituted Subazaporphyrins. Chem Eur J 2008, 14, 1342. <http://dx.doi.org/10.1002/chem.200701542>
  • Hill Thomas J., Hughes Richard K., Scott Lawrence T.: Steps toward the synthesis of a geodesic C60H12 end cap for a C3v carbon [6,6]nanotube. Tetrahedron 2008, 64, 11360. <http://dx.doi.org/10.1016/j.tet.2008.09.087>
  • Kawase Takeshi, Nishiyama Yoshitaka, Nakamura Takamitsu, Ebi Takahiro, Matsumoto Kouzou, Kurata Hiroyuki, Oda Masaji: Cyclic [5]Paraphenyleneacetylene: Synthesis, Properties, and Formation of a Ring-in-Ring Complex Showing a Considerably Large Association Constant and Entropy Effect. Angew Chem 2007, 119, 1104. <http://dx.doi.org/10.1002/ange.200603707>
  • Kawase Takeshi, Nishiyama Yoshitaka, Nakamura Takamitsu, Ebi Takahiro, Matsumoto Kouzou, Kurata Hiroyuki, Oda Masaji: Cyclic [5]Paraphenyleneacetylene: Synthesis, Properties, and Formation of a Ring-in-Ring Complex Showing a Considerably Large Association Constant and Entropy Effect. Angew Chem Int Ed 2007, 46, 1086. <http://dx.doi.org/10.1002/anie.200603707>
  • Amsharov K.Yu., Jansen M.: Formation of fullerenes by pyrolysis of perchlorofulvalene and its derivatives. Carbon 2007, 45, 117. <http://dx.doi.org/10.1016/j.carbon.2006.07.019>
  • Treitel Noach, Sheradsky Tuvia, Peng Lingqing, Scott Lawrence T., Rabinovitz Mordecai: C30H126−: Self-Aggregation, High Charge Density, and Pyramidalization in a Supramolecular Structure of a Supercharged Hemifullerene. Angew Chem 2006, 118, 3351. <http://dx.doi.org/10.1002/ange.200503542>
  • Treitel Noach, Sheradsky Tuvia, Peng Lingqing, Scott Lawrence T., Rabinovitz Mordecai: C30H126−: Self-Aggregation, High Charge Density, and Pyramidalization in a Supramolecular Structure of a Supercharged Hemifullerene. Angew Chem Int Ed 2006, 45, 3273. <http://dx.doi.org/10.1002/anie.200503542>
  • Tsefrikas Vikki M., Arns Steve, Merner Patrick M., Warford C. Chad, Merner Bradley L., Scott Lawrence T., Bodwell Graham J.: Benzo[a]acecorannulene:  Surprising Formation of a New Bowl-Shaped Aromatic Hydrocarbon from an Attempted Synthesis of 1,2-Diazadibenzo[d,m]corannulene. Org Lett 2006, 8, 5195. <http://dx.doi.org/10.1021/ol061554v>
  • Satoh Hiroyasu, Yamamoto Gaku, Mazaki Yasuhiro: Synthesis and Properties of Trispiro[truxenetris(cycloalkane)]s. Bull Chem Soc Jpn 2006, 79, 938. <http://dx.doi.org/10.1246/bcsj.79.938>
  • Sygula Andrzej, Sygula Renata, Rabideau Peter W.: Barrelene–semibullvalene rearrangement induced by visible light: synthesis of dicorannulenosemibullvalene dimethyl dicarboxylate. Tetrahetron Lett 2005, 46, 1189. <http://dx.doi.org/10.1016/j.tetlet.2004.12.053>
  • Petrukhina Marina A., Scott Lawrence T.: Coordination chemistry of buckybowls: from corannulene to a hemifullerene. Dalton Trans 2005, 2969. <http://dx.doi.org/10.1039/b504317d>
  • Petrukhina Marina A., Andreini Kristian W., Peng Lingqing, Scott Lawrence T.: Hemibuckminsterfullerene C30H12: X-ray Crystal Structures of the Parent Hydrocarbon and of the Two-Dimensional Organometallic Network {[Rh2(O2CCF3)4]3⋅(C30H12)}. Angew Chem 2004, 116, 5593. <http://dx.doi.org/10.1002/ange.200460855>
  • Petrukhina Marina A., Andreini Kristian W., Peng Lingqing, Scott Lawrence T.: Hemibuckminsterfullerene C30H12: X-ray Crystal Structures of the Parent Hydrocarbon and of the Two-Dimensional Organometallic Network {[Rh2(O2CCF3)4]3⋅(C30H12)}. Angew Chem Int Ed 2004, 43, 5477. <http://dx.doi.org/10.1002/anie.200460855>
  • Gilbertson Robert D, Wu He-Ping, Gorman-Lewis Drew, Weakley Timothy J.R, Weiss Hans-Christoph, Boese Roland, Haley Michael M: An unusually robust triple bond: synthesis, structure and reactivity of 3-alkynylcyclopropenes. Tetrahedron 2004, 60, 1215. <http://dx.doi.org/10.1016/j.tet.2003.11.074>
  • Priyakumar U.Deva, Punnagai M., Krishna Mohan G.P., Sastry G.Narahari: A computational study of cation–π interactions in polycyclic systems: exploring the dependence on the curvature and electronic factors. Tetrahedron 2004, 60, 3037. <http://dx.doi.org/10.1016/j.tet.2004.01.086>
  • Makowski Mariusz, Makowska Joanna, Chmurzy��ski Lech, Deva Priyakumar U., Narahari Sastry G., Rudyk R, Molina M.A.A, G��mez M.I, Blanco S.E, Ferretti F.H: Ab initio study of the energetics of protonation, deprotonation and homocomplexed cations and anions formation in systems modeling side chains of biomolecules. Journal of Molecular Structure: THEOCHEM 2004, 674, 61. <http://dx.doi.org/10.1016/j.theochem.2004.01.003>
  • Morita Yasushi, Nishida Shinsuke, Kobayashi Tadahiro, Fukui Kozo, Sato Kazunobu, Shiomi Daisuke, Takui Takeji, Nakasuji Kazuhiro: The First Bowl-Shaped Stable Neutral Radical with a Corannulene System:  Synthesis and Characterization of the Electronic Structure. Org Lett 2004, 6, 1397. <http://dx.doi.org/10.1021/ol0497786>
  • Dinadayalane T.C., Sastry G.Narahari: Isolated pentagon rule in buckybowls: a computational study on thermodynamic stabilities and bowl-to-bowl inversion barriers. Tetrahedron 2003, 59, 8347. <http://dx.doi.org/10.1016/j.tet.2003.09.007>
  • Priyakumar U.Deva, Sastry G.Narahari: Cation-π interactions of curved polycyclic systems: M+ (M=Li and Na) ion complexation with buckybowls. Tetrahetron Lett 2003, 44, 6043. <http://dx.doi.org/10.1016/S0040-4039(03)01512-0>
  • de Mello Castanho Amboni Renata Dias, da Silva Junkes Berenice, Heinzen Vilma Edite Fonseca, Yunes Rosendo Augusto, Dinadayalane T.C, Narahari Sastry G, Zhao Dong-Xia, Yang Zhong-Zhi: Semi-empirical topological method for prediction of the chromatographic retention of esters. Journal of Molecular Structure: THEOCHEM 2002, 579, 53. <http://dx.doi.org/10.1016/S0166-1280(01)00716-3>
  • Nishinaga Tohru, Inoue Ryota, Matsuura Akira, Komatsu Koichi: Formation of a Novel Arenium Ion from the Radical Cation of a Twisted Triphenylene Fully Annelated with Bicyclo[2.2.2]octene Units. Org Lett 2002, 4, 1435. <http://dx.doi.org/10.1021/ol0255662>
  • Gómez-Lor Berta, Frutos Óscar de, Ceballos Plácido A., Granier Thierry, Echavarren Antonio M.: Synthesis of NewC3h andC3v Truxene Derivatives. Eur J Org Chem 2001, 2001, 2107. <http://dx.doi.org/10.1002/1099-0690(200106)2001:11<2107::AID-EJOC2107>3.0.CO;2-F>
  • Tobe Yoshito, Nakagawa Nobuko, Kishi Jun-ya, Sonoda Motohiro, Naemura Koichiro, Wakabayashi Tomonari, Shida Tadamasa, Achiba Yohji: Polyyne cyclization to form carbon cages: [16.16.16](1,3,5)cyclophanetetracosayne derivatives C60H6 and C60Cl6 as precursors to C60 fullerene. Tetrahedron 2001, 57, 3629. <http://dx.doi.org/10.1016/S0040-4020(01)00250-2>
  • Sygula Andrzej, Xu Guopin, Marcinow Zbigniew, Rabideau Peter W: ‘Buckybowls’—introducing curvature by solution phase synthesis. Tetrahedron 2001, 57, 3637. <http://dx.doi.org/10.1016/S0040-4020(01)00251-4>
  • Dinadayalane T.C, Sastry G.Narahari: Synthetic strategies toward buckybowls and C60: benzannulation is remarkably facile compared to cyclopentannulation. Tetrahetron Lett 2001, 42, 6421. <http://dx.doi.org/10.1016/S0040-4039(01)01268-0>
  • Dinadayalane T.C, Deva Priyakumar U, Narahari Sastry G, Yu Xin, Li Shen-Min, Xu Zhen-Feng, Li Ze-Sheng, Sun Chia-Chung, Ceotto M, Gianturco F.A: Theoretical studies on the effect of sequential benzannulation to corannulene. Journal of Molecular Structure: THEOCHEM 2001, 543, 1. <http://dx.doi.org/10.1016/S0166-1280(00)00823-X>
  • Marsella Michael J., Yoon Kunsang, Tham Fook S.: Synthesis and Crystal Structure of a Tubular Sexithiophene. Org Lett 2001, 3, 2129. <http://dx.doi.org/10.1021/ol016122t>
  • Preda Dorin V, Scott Lawrence T: Addition of dihalocarbenes to corannulene. A fullerene-type reaction. Tetrahetron Lett 2000, 41, 9633. <http://dx.doi.org/10.1016/S0040-4039(00)01734-2>