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Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

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Polyarenes I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 349))

Abstract

This chapter summarizes the synthesis, physical properties, structure, and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of polynuclear aromatic compounds between the closed-shell fullerenes and the flat extended arrays of graphene. These warped sheets can be seen as fragments of fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature endows them with physical properties distinct from flat polynuclear hydrocarbons, which opens up unique possibilities for molecular bowls in various organic materials applications.

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References

  1. Beck A, Bleicher MN, Crowe DW (1969) Excursions into mathematics. Worth, New York

    Google Scholar 

  2. Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE (1985) Nature 318:162–163

    CAS  Google Scholar 

  3. Iijima S (1991) Nature 354:56

    CAS  Google Scholar 

  4. Petrukhina MA, Scott LT (eds) (2011) Fragments of fullerenes and carbon nanotubes: designed synthesis, unusual reactions, and coordination chemistry. Wiley, Hoboken

    Google Scholar 

  5. Sygula A (2011) Eur J Org Chem 1611–1625

    Google Scholar 

  6. Tsefrikas VM, Scott LT (2006) Chem Rev 106:4868–4884

    CAS  Google Scholar 

  7. Wu YT, Siegel JS (2006) Chem Rev 106:4843–4867

    CAS  Google Scholar 

  8. Sygula A, Rabideau PW (2006) In: Haley MM, Tykwinski RR (eds) Carbon-rich compounds: from molecules to materials. Willey, Weinheim, pp 529–565

    Google Scholar 

  9. Scott LT (2004) Angew Chem Int Ed 43:4994–5007

    CAS  Google Scholar 

  10. Scott LT, Bronstein HE, Preda DV, Ansems RBM, Bratcher MS, Hagen S (1999) Pure Appl Chem 71:209–219

    CAS  Google Scholar 

  11. Mehta G, Rao HSP (1998) Tetrahedron 54:13325–13370

    CAS  Google Scholar 

  12. Schmidt BM, Lentz D (2014) Chem Lett 43:171–177

    CAS  Google Scholar 

  13. Amaya T, Hirao T (2012) Pure Appl Chem 84:1089–1100

    CAS  Google Scholar 

  14. Higashibayashi S, Sakurai H (2011) Chem Lett 40:122–128

    CAS  Google Scholar 

  15. Amaya T, Hirao T (2011) Chem Commun 47:10524–10535

    CAS  Google Scholar 

  16. Reisch HA, Bratcher MS, Scott LT (2000) Org Lett 2:1427–1430

    CAS  Google Scholar 

  17. Barth WE, Lawton RG (1966) J Am Chem Soc 88:380–381

    CAS  Google Scholar 

  18. Barth WE, Lawton RG (1971) J Am Chem Soc 93:1730–1745

    Google Scholar 

  19. Hopf H (2000) Classics in hydrocaron chemistry. Wiley, Weinheim, p 331

    Google Scholar 

  20. Scott LT, Hashemi MM, Meyer DT, Warren HB (1991) J Am Chem Soc 113:7082–7084

    CAS  Google Scholar 

  21. Scott LT, Cheng PC, Hashemi MM, Bratcher MS, Meyer DT, Warren HB (1997) J Am Chem Soc 119:10963–10968

    CAS  Google Scholar 

  22. Brown RFC, Harrington KJ, McMullen GL (1974) J Chem Soc Chem Commun 123–124

    Google Scholar 

  23. Brown RFC, Eastwood FW, Harrington KJ, McMullen GL (1974) Aust J Chem 27:2391–2402

    Google Scholar 

  24. Brown RFC, Eastwood FW, Jackman GP (1977) Aust J Chem 30:1757–1767

    CAS  Google Scholar 

  25. Marcinow Z, Grove DI, Rabideau PW (2002) J Org Chem 67:3537–3539

    CAS  Google Scholar 

  26. Sygula A, Karlen SD, Sygula R, Rabideau PW (2002) Org Lett 4:3135–3137

    CAS  Google Scholar 

  27. Wu YT, Hayama T, Baldrige KK, Linden A, Siegel JS (2006) J Am Chem Soc 128:6870–6884

    CAS  Google Scholar 

  28. Kung YH, Cheng YS, Tai CC, Liu WS, Shin CC, Ma CC, Tsai YC, Wu TC, Kuo MY, Wu YT (2010) Chem Eur J 16:5909–5919

    CAS  Google Scholar 

  29. Elliott EL, Orita A, Hasegawa D, Gantzel P, Otera J, Siegel JS (2005) Org Biomol Chem 3:581–583

    CAS  Google Scholar 

  30. Albright LF, Crynes BL (eds) (1976) Industrial and laboratory pyrolyses, ACS Symposium Series 32. American Chemical Society, Washington

    Google Scholar 

  31. Borchardt A, Fuchicello A, Kilway KV, Baldridge KK, Siegel JS (1992) J Am Chem Soc 114:1921–1923

    CAS  Google Scholar 

  32. Seiders TJ, Baldridge KK, Siegel JS (1996) J Am Chem Soc 118:2754–2755

    CAS  Google Scholar 

  33. Olah GA, Prakash GKS (1976) Synthesis 607–608

    Google Scholar 

  34. Seiders TJ, Elliott EL, Grube GH, Siegel JS (1999) J Am Chem Soc 121:7804–7813

    CAS  Google Scholar 

  35. Sygula A, Rabideau PW (1999) J Am Chem Soc 121:7800–7803

    CAS  Google Scholar 

  36. Sygula A, Rabideau PW (2000) J Am Chem Soc 122:6323–6324

    CAS  Google Scholar 

  37. Xu G, Sygula A, Marcinow Z, Rabideau PW (2000) Tetrahedron Lett 41:9931–9934

    CAS  Google Scholar 

  38. Sygula A, Xu G, Marcinow Z, Rabideau PW (2001) Tetrahedron 57:3637–3644

    CAS  Google Scholar 

  39. Wu YT, Bandera D, Maag R, Linden A, Baldridge KK, Siegel JS (2008) J Am Chem Soc 130:10729–10739

    CAS  Google Scholar 

  40. Schmidt BM, Topolinski B, Yamada M, Higashibayashi S, Shionoya M, Sakurai H, Lentz D (2013) Chem Eur J 19:13872–13880

    CAS  Google Scholar 

  41. Schmidt BM, Seki S, Topolinski B, Ohkubo K, Fukuzumi S, Sakurai H, Lentz D (2012) Angew Chem Int Ed 51:11385–11388

    CAS  Google Scholar 

  42. Stanger A, Ashkenazi N, Boese R, Bläser D, Stellberg P (1997) Chern Eur J 3:208–211

    CAS  Google Scholar 

  43. Butterfield AM, Gilomen B, Siegel JS (2012) Org Process Res Dev 16:664–676

    CAS  Google Scholar 

  44. Duttwyler S, Butterfield AM, Siegel JS (2013) J Org Chem 78:2134–2138

    CAS  Google Scholar 

  45. Greene AK, Scott LT (2013) J Org Chem 78:2139–2143

    CAS  Google Scholar 

  46. Sygula A, Sygula R, Fronczek FR, Rabideau PW (2002) J Org Chem 67:6487–6492

    CAS  Google Scholar 

  47. Nishida S, Morita Y, Ueda A, Kobayashi T, Fukui K, Ogasawara K, Sato K, Takui T, Nakasuji K (2008) J Am Chem Soc 130:14954–14955

    CAS  Google Scholar 

  48. Preda DV (2001) Ph.D. Dissertation, Boston College, Chestnut Hill

    Google Scholar 

  49. Cheng PC (1996) Ph.D. Dissertation, Boston College, Chestnut Hill

    Google Scholar 

  50. Topolinski B, Schmidt BM, Kathan M, Troyanov SI, Lentz D (2012) Chem Commun 48:6298–6300

    CAS  Google Scholar 

  51. Scott LT, Hashemi MM, Bratcher MS (1992) J Am Chem Soc 114:1920–1921

    CAS  Google Scholar 

  52. Morita Y, Nishida S, Kobayashi T, Fukui K, Sato K, Shiomi D, Takui T, Nakasuji K (2004) Org Lett 6:1397–1400

    CAS  Google Scholar 

  53. Jones CS, Elliott E, Siegel JS (2004) Synlett 187–192

    Google Scholar 

  54. Sygula A, Sygula R, Rabideau PW (2005) Org Lett 7:4999–5001

    CAS  Google Scholar 

  55. Yanney M, Fronczek FR, Henry WP, Beard DJ, Sygula A (2011) Eur J Org Chem 6636–6639

    Google Scholar 

  56. Yanney M, Fronczek FR, Sygula A (2012) Org Lett 14:4942–4945

    CAS  Google Scholar 

  57. Seiders TJ, Baldridge KK, Grube GH, Siegel JS (2001) J Am Chem Soc 123:517–525

    CAS  Google Scholar 

  58. Haddon RC, Scott LT (1986) Pure Appl Chem 58:137–142

    CAS  Google Scholar 

  59. Haddon RC (1988) Acc Chem Res 21:243–249

    CAS  Google Scholar 

  60. Haddon RC (1993) Science 261:1545–1550

    CAS  Google Scholar 

  61. Sygula A, Abdourazak AH, Rabideau PW (1996) J Am Chem Soc 118:339–343

    CAS  Google Scholar 

  62. Seiders TJ, Baldridge KK, Elliott EL, Grube GH, Siegel JS (1999) J Am Chem Soc 121:7439–7440

    CAS  Google Scholar 

  63. Hanson JC, Nordman CE (1976) Acta Crystallogr B32:1147–1153

    CAS  Google Scholar 

  64. Petrukhina MA, Andreini KW, Mack J, Scott LT (2005) J Org Chem 70:5713–5716

    CAS  Google Scholar 

  65. Fedurco M, Olmstead MM, Fawcett WR (1995) Inorg Chem 34:390–392

    CAS  Google Scholar 

  66. Dawe LN, AlHujran TA, Tran HA, Mercer JI, Jackson EA, Scott LT, Georghiou PE (2012) Chem Commun 48:5563–5565

    CAS  Google Scholar 

  67. Juríček M, Strutt NL, Barnes JC, Butterfield AM, Dale EJ, Baldridge KK, Stoddart JF, Siegel JS (2014) Nat Chem 6:222

    Google Scholar 

  68. Bruno C, Benassi R, Passalacqua A, Paolucci F, Fontanesi C, Marcaccio M, Jackson EA, Scott LT (2009) J Phys Chem B 113:1954–1962

    CAS  Google Scholar 

  69. Valenti G, Bruno C, Rapino S, Fiorani A, Jackson EA, Scott LT, Paolucci F, Marcaccio M (2010) J Phys Chem C 114:19467–19472

    CAS  Google Scholar 

  70. Hayama T, Baldridge KK, Wu YT, Linden A, Siegel JS (2008) J Am Chem Soc 130:1583–1591

    CAS  Google Scholar 

  71. Baldridge KK, Siegel JS (2008) Theor Chem Acc 120:95–106

    CAS  Google Scholar 

  72. Samdal S, Hedberg L, Hedberg K, Richardson AD, Bancu M, Scott LT (2003) J Phys Chem A 107:411–417

    CAS  Google Scholar 

  73. Hayama T, Wu YT, Linden A, Baldridge KK, Siegel JS (2007) J Am Chem Soc 129:12612–12613

    CAS  Google Scholar 

  74. Zhang Q, Kawasumi K, Segawa Y, Itami K, Scott LT (2012) J Am Chem Soc 134:15664–15667

    CAS  Google Scholar 

  75. Baldridge KK, Hardcastle KI, Seiders TJ, Siegel JS (2010) Org Biomol Chem 8:53–55

    CAS  Google Scholar 

  76. Ayalon A, Rabinovitz M, Cheng PC, Scott LT (1992) Angew Chem Int Ed Engl 31:1636–1637

    Google Scholar 

  77. Filatov AS, Sumner NJ, Spisak SN, Zabula AV, Rogachev AY, Petrukhina MA (2012) Chem Eur J 18:15753–15760

    CAS  Google Scholar 

  78. Seiders TJ, Baldridge KK, Siegel JS, Gleiter R (2000) Tetrahedron Lett 41:4519–4522

    CAS  Google Scholar 

  79. Morita Y, Ueda A, Nishida S, Fukui K, Ise T, Shiomi D, Sato K, Takui T, Nakasuji K (2008) Angew Chem Int Ed 47:2035–2038

    CAS  Google Scholar 

  80. Sevryugina Y, Rogachev AY, Jackson EA, Scott LT, Petrukhina MA (2006) J Org Chem 71:6615–6618

    CAS  Google Scholar 

  81. Kuvychko IV, Spisak SN, Chen YS, Popov AA, Petrukhina MA, Strauss SH, Boltalina OV (2012) Angew Chem Int Ed 51:4939–4942

    CAS  Google Scholar 

  82. Eliseeva MN, Scott LT (2012) J Am Chem Soc 134:15169–15172

    CAS  Google Scholar 

  83. Grube GH, Elliott EL, Steffens RJ, Jones CS, Baldridge KK, Siegel JS (2003) Org Lett 5:713–716

    CAS  Google Scholar 

  84. Mattarella M, Siegel JS (2012) Org Biomol Chem 10:5799–5802

    CAS  Google Scholar 

  85. Eberhard MR, Wang Z, Jensen CM (2002) Chem Commun 818–819

    Google Scholar 

  86. Grasa GA, Nolan SP (2001) Org Lett 3:119–122

    CAS  Google Scholar 

  87. Wu YL, Stuparu MC, Boudon C, Gisselbrecht JP, Schweizer WB, Baldridge KK, Siegel JS, Diederich F (2012) J Org Chem 77:11014–11026

    CAS  Google Scholar 

  88. Littke AF, Fu GC (1998) Angew Chem Int Ed 37:3387–3388

    CAS  Google Scholar 

  89. Jackson EA, Steinberg BD, Bancu M, Wakamiya A, Scott LT (2007) J Am Chem Soc 129:484–485

    CAS  Google Scholar 

  90. Pappo D, Mejuch T, Reany O, Solel E, Gurram M, Keinan E (2009) Org Lett 11:1063–1066

    CAS  Google Scholar 

  91. Mizyed S, Georghiou PE, Bancu M, Cuadra B, Rai AK, Cheng P, Scott LT (2001) J Am Chem Soc 123:12770–12774

    CAS  Google Scholar 

  92. Buncel E, Crampton MR, Strauss TJ, Terrier F (1984) Electron deficient aromatic and heteroaromatic-base interactions: the chemistry of anionic sigma complexes. Elsevier, New York

    Google Scholar 

  93. Pogoreltsev A, Solel E, Pappo D, Keinan E (2012) Chem Commun 48:5425–5427

    CAS  Google Scholar 

  94. Gershoni-Poranne R, Pappo D, Solel E, Keinan E (2009) Org Lett 11:5146–5149

    CAS  Google Scholar 

  95. Mattarella M, Berstis L, Baldridge KK, Siegel JS (2014) Bioconjugate Chem 25:115–128

    CAS  Google Scholar 

  96. Mattarella M, Haberl JM, Ruokolainen J, Landau EM, Mezzenga R, Siegel JS (2013) Chem Commun 49:7204–7206

    CAS  Google Scholar 

  97. Stuparu MC (2012) J Polym Sci A Polym Chem 50:2641–2649

    CAS  Google Scholar 

  98. Butterfield A (2008) M.S. Thesis, University of Zurich, Zurich

    Google Scholar 

  99. Huang R, Huang W, Wang Y, Tang Z, Zheng L (1997) J Am Chem Soc 119:5954–5955

    CAS  Google Scholar 

  100. Bancu M, Rai AK, Cheng PC, Gilardi RD, Scott LT (2004) Synlett 173–176

    Google Scholar 

  101. Miyajima D, Tashiro K, Araoka F, Takezoe H, Kim J, Kato K, Takata M, Aida T (2009) J Am Chem Soc 131:44–45

    CAS  Google Scholar 

  102. Ham JS (1953) J Chem Phys 21:756

    CAS  Google Scholar 

  103. Dey J, Will AY, Agbaria RA, Rabideau PW, Abdourazak AH, Sygula R, Warner IM (1997) J Fluoresc 7:231–236

    CAS  Google Scholar 

  104. Ueda A, Ogasawara K, Nishida S, Ise T, Yoshino T, Nakazawa S, Sato K, Takui T, Nakasuji K, Morita Y (2010) Angew Chem Int Ed 49:6333–6337

    CAS  Google Scholar 

  105. Ueda A, Nishida S, Fukui K, Ise T, Shiomi D, Sato K, Takui T, Nakasuji K, Morita Y (2010) Angew Chem Int Ed 49:1678–1682

    CAS  Google Scholar 

  106. Abdourazak AH, Sygula A, Rabideau PW (1993) J Am Chem Soc 115:3010–3011

    CAS  Google Scholar 

  107. Sygula A, Sygula R, Rabideau PW (2006) Org Lett 8:5909–5911

    CAS  Google Scholar 

  108. Sygula A, Fronczek FR, Sygula R, Rabideau PW, Olmstead MM (2007) J Am Chem Soc 129:3842–3843

    CAS  Google Scholar 

  109. Furrer F, Linden A, Stuparu MC (2013) Chem Eur J 19:13199–13206

    CAS  Google Scholar 

  110. Schmidt BM, Topolinski B, Roesch P, Lentz D (2012) Chem Commun 48:6520–6522

    CAS  Google Scholar 

  111. Kuvychko IV, Dubceac C, Deng SHM, Wang XB, Granovsky AA, Popov AA, Petrukhina MA, Strauss SH, Boltalina OV (2013) Angew Chem Int Ed 52:7505–7508

    CAS  Google Scholar 

  112. Sygula A, Folsom HE, Sygula R, Abdourazak AH, Marcinow Z, Fronczek FR, Rabideau PW (1994) J Chem Soc Chem Commun 2571–2572

    Google Scholar 

  113. Sygula A, Rabideau PW (1994) J Chem Soc Chem Commun 1497–1499

    Google Scholar 

  114. Steffens RJ, Baldridge KK, Siegel JS (2000) Helv Chim Acta 83:2644–2654

    CAS  Google Scholar 

  115. McMahon BJ (1997) B.S. Thesis, Boston College, Chestnut Hill

    Google Scholar 

  116. Peng L, Scott LT (2005) J Am Chem Soc 127:16518–16521

    CAS  Google Scholar 

  117. Bratcher MS (1996) Ph.D. Dissertation, Boston College, Chestnut Hill

    Google Scholar 

  118. Wu YT, Linden A, Siegel JS (2005) Org Lett 7:4353–4355

    CAS  Google Scholar 

  119. Marcinow Z, Sygula A, Ellern A, Rabideau PW (2001) Org Lett 3:3527–3529

    CAS  Google Scholar 

  120. Shi K, Lei T, Wang XY, Wang JY, Pei J (2014) Chem Sci 5:1041–1045

    CAS  Google Scholar 

  121. Weitz A, Shabtai E, Rabinovitz M, Bratcher MS, McComas CC, Best MD, Scott LT (1998) Chem Eur J 4:234–239

    CAS  Google Scholar 

  122. Tsefrikas VM, Arns S, Merner PM, Warford CC, Merner BL, Scott LT, Bodwell GJ (2006) Org Lett 8:5195–5198

    CAS  Google Scholar 

  123. Filatov AS, Ferguson MV, Spisak SN, Li B, Campana CF, Petrukhina MA (2014) Cryst Growth Des 14:756–762

    CAS  Google Scholar 

  124. Rai AK (1996) M.S. Thesis, Boston College, Chestnut Hill

    Google Scholar 

  125. Wegner HA, Scott LT, de Meijere A (2003) J Org Chem 68:883–887

    CAS  Google Scholar 

  126. Allemann O, Duttwyler S, Romanato P, Baldridge KK, Siegel JS (2011) Science 332:574–577

    CAS  Google Scholar 

  127. Vollhardt KPC (1977) Acc Chem Res 10:1–8

    CAS  Google Scholar 

  128. Steinberg BD, Jackson EA, Filatov AS, Wakamiya A, Petrukhina MA, Scott LT (2009) J Am Chem Soc 131:10537–10545

    CAS  Google Scholar 

  129. Seiders TJ, Baldridge KK, Siegel JS (2001) Tetrahedron 57:3737–3742

    CAS  Google Scholar 

  130. Rabideau PW, Abdourazak AH, Folsom HE, Marcinow Z, Sygula A, Sygula R (1994) J Am Chem Soc 116:7891–7892

    CAS  Google Scholar 

  131. Clayton MD, Marcinow Z, Rabideau PW (1996) J Org Chem 61:6052–6054

    CAS  Google Scholar 

  132. Sygula A, Marcinow Z, Fronczek FR, Guzei I, Rabideau PW (2000) Chem Commun 2439–2400

    Google Scholar 

  133. Mehta G, Shahk SR, Ravikumarc K (1993) J Chem Soc Chem Commun 1006–1008

    Google Scholar 

  134. Sakurai H, Daiko T, Hirao T (2003) Science 301:1878

    CAS  Google Scholar 

  135. Sastry GN, Jemmis ED, Mehta G, Shah SR (1993) J Chem Soc Perkin Trans 2:1867–1871

    Google Scholar 

  136. Sakurai H, Daiko T, Sakane H, Amaya T, Hirao T (2005) J Am Chem Soc 127:11580–11581

    CAS  Google Scholar 

  137. Amaya T, Sakane H, Muneishi T, Hirao T (2008) Chem Commun 765–767

    Google Scholar 

  138. Amaya T, Mori K, Wu HL, Ishida S, Nakamura J, Murata K, Hirao T (2007) Chem Commun 1902–1904

    Google Scholar 

  139. Amaya T, Hifumi M, Okada M, Shimizu Y, Moriuchi T, Segawa K, Ando Y, Hirao T (2011) J Org Chem 76:8049–8052

    CAS  Google Scholar 

  140. Schmidt BM, Topolinski B, Higashibayashi S, Kojima T, Kawano M, Lentz D, Sakurai H (2013) Chem Eur J 19:3282–3286

    CAS  Google Scholar 

  141. Chen JJ, Onogi S, Hsieh YC, Hsiao CC, Higashibayashi S, Sakurai H, Wu YT (2012) Adv Synth Calal 354:1551–1558

    CAS  Google Scholar 

  142. Higashibayashi S, Onogi S, Srivastava HK, Sastry GN, Wu YT, Sakurai H (2013) Angew Chem Int Ed 52:7314–7316

    CAS  Google Scholar 

  143. Higashibayashi S, Baig RBN, Morita Y, Sakurai H (2012) Chem Lett 41:84–86

    CAS  Google Scholar 

  144. Shrestha BB, Karanjit S, Panda G, Higashibayashi S, Sakurai H (2013) Chem Lett 42:386–388

    CAS  Google Scholar 

  145. Higashibayashi S, Sakurai H (2008) J Am Chem Soc 130:8592–8593

    CAS  Google Scholar 

  146. Higashibayashi S, Sakurai H (2007) Chem Lett 36:18–19

    CAS  Google Scholar 

  147. Reza AFGM, Higashibayashi S, Sakurai H (2009) Chem Asian J 4:1329–1337

    CAS  Google Scholar 

  148. Higashibayashi S, Reza AFGM, Sakurai H (2010) J Org Chem 75:4626–4628

    CAS  Google Scholar 

  149. Tsuruoka R, Higashibayashi S, Ishikawa T, Toyota S, Sakurai H (2010) Chem Lett 39:646–647

    CAS  Google Scholar 

  150. Imamura K, Takimiya K, Otsubo T, Aso Y (1999) Chem Commun 1859–1860

    Google Scholar 

  151. Furukawa S, Kobayashi J, Kawashima T (2009) J Am Chem Soc 131:14192–14193

    CAS  Google Scholar 

  152. Higashibayashi S, Tsuruoka R, Soujanya Y, Purushotham U, Sastry GN, Seki S, Ishikawa T, Toyota S, Sakurai H (2012) Bull Chem Soc Jpn 85:450–467

    CAS  Google Scholar 

  153. Tan Q, Higashibayashi S, Karanjit S, Sakurai H (2012) Nature Commun 3:891

    Google Scholar 

  154. Amaya T, Seki S, Moriuchi T, Nakamoto K, Nakata T, Sakane H, Saeki A, Tagawa S, Hirao T (2009) J Am Chem Soc 131:408–409

    CAS  Google Scholar 

  155. Morita Y, Nakao S, Haesuwannakij S, Higashibayashi S, Sakurai H (2012) Chem Commun 48:9050–9052

    CAS  Google Scholar 

  156. Amaya T, Nakata T, Hirao T (2009) J Am Chem Soc 131:10810–10811

    CAS  Google Scholar 

  157. Abdourazak AH, Marcinow Z, Sygula A, Sygula R, Rabideau PW (1995) J Am Chem Soc 117:6410–6411

    CAS  Google Scholar 

  158. Hagen S, Bratcher MS, Erickson MS, Zimmermann G, Scott LT (1997) Angew Chem Int Ed 36:406–408

    CAS  Google Scholar 

  159. Petrukhina MA, Andreini KW, Peng L, Scott LT (2004) Angew Chem Int Ed 43:5477–5481

    CAS  Google Scholar 

  160. Gallego M, Calbo J, Aragó J, Calderon RMK, Liquido FH, Iwamoto T, Greene AK, Jackson EA, Pérez EM, Ortí E, Guldi DM, Scott LT, Martín N (2014) Angew Chem Int Ed 53:2170–2175

    CAS  Google Scholar 

  161. Clayton MD, Rabideau PW (1997) Tetrahedron Lett 38:741–744

    CAS  Google Scholar 

  162. Wu TC, Hsin HJ, Kuo MY, Li CH, Wu YT (2011) J Am Chem Soc 133:16319–16321

    CAS  Google Scholar 

  163. Hsiao CC, Lin YK, Liu CJ, Wu TC, Wu YT (2010) Adv Synth Catal 352:3267–3274

    CAS  Google Scholar 

  164. Chen MK, Hsin HJ, Wu TC, Kang BY, Lee YW, Kuo MY, Wu YT (2014) Chem Eur J 20:598–608

    CAS  Google Scholar 

  165. Scott LT, Bratcher MS, Hagen S (1996) J Am Chem Soc 118:8743–8744

    CAS  Google Scholar 

  166. Ansems RBM, Scott LT (2000) J Am Chem Soc 122:2719–2724

    CAS  Google Scholar 

  167. Forkey DM, Attar S, Noll BC, Koerner R, Olmstead MM, Balch AL (1997) J Am Chem Soc 119:5766–5767

    CAS  Google Scholar 

  168. Wang L, Shevlin PB (2000) Org Lett 2:3703–3705

    CAS  Google Scholar 

  169. Amsharov KY, Kabdulov MA, Jansen M (2012) Angew Chem Int Ed 51:4594–4597

    CAS  Google Scholar 

  170. Bronstein HE, Choi N, Scott LT (2002) J Am Chem Soc 124:8870–8875

    CAS  Google Scholar 

  171. Chang HI, Huang HT, Huang CH, Kuo MY, Wu YT (2010) Chem Commun 46:7241–7243

    CAS  Google Scholar 

  172. Biedermann PU, Pogodin S, Agranat I (1999) J Org Chem 64:3655–3662

    CAS  Google Scholar 

  173. Bronstein HE, Scott LT (2008) J Org Chem 73:88–93

    CAS  Google Scholar 

  174. Wegner HA, Reisch H, Rauch K, Demeter A, Zachariasse KA, de Meijere A, Scott LT (2006) J Org Chem 71:9080–9087

    CAS  Google Scholar 

  175. Fowler PW, Manolopoulos DE (2006) An atlas of fullerenes. Dover Publications, Mineola

    Google Scholar 

  176. Thilgen C, Herrmann A, Diederich F (1997) Angew Chem Int Ed 36:2268–2280

    CAS  Google Scholar 

  177. Wu TC, Chen MK, Lee YW, Kuo MY, Wu YT (2013) Angew Chem Int Ed 53:1289–1293

    Google Scholar 

  178. Whalley AC, Plunkett KN, Gorodetsky AA, Schenck CL, Chiu CY, Steigerwald ML, Nuckolls C (2011) Chem Sci 2:132–135

    CAS  Google Scholar 

  179. Baldridge KK, Siegel JS (1997) Theoret Chem Acc 97:67–71

    CAS  Google Scholar 

  180. Scott LT, Jackson EA, Zhang Q, Steinberg BD, Bancu M, Li B (2012) J Am Chem Soc 134:107–110

    CAS  Google Scholar 

  181. Kawasumi K, Zhang Q, Segawa Y, Scott LT, Itami K (2013) Nat Chem 5:739–744

    CAS  Google Scholar 

  182. Filatov AS, Scott LT, Petrukhina MA (2010) Cryst Growth Des 10:4607–4621

    CAS  Google Scholar 

  183. Yamada N, Ueno K, Nishimura J, Okada Y (2010) Patent US 7,794,854 B2

    Google Scholar 

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Correspondence to Yao-Ting Wu or Jay S. Siegel .

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Wu, YT., Siegel, J.S. (2014). Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons. In: Siegel, J., Wu, YT. (eds) Polyarenes I. Topics in Current Chemistry, vol 349. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2014_548

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