Skip to main content
Springer Nature Link
Log in

Quinodimethanes Incorporated in Non-Benzenoid Aromatic or Antiaromatic Frameworks

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

Three isomers of quinodimethanes (QDMs) adopt different electronic configurations and geometries, generating their own characteristic physical properties. Incorporation of QDMs into non-benzenoid aromatic or antiaromatic frameworks not only planarizes the whole π system optimizing conjugation, but also changes the electronic properties inherent to QDMs, sometimes drastically, due to the topology of the π system, through interaction with the remaining part of the molecules. In non-benzenoid systems, molecular orbital levels and orbital distribution are uneven compared to benzenoid systems, thereby polarizing the ground state and leading to unique behavior in excited states. In antiaromatic systems, open-shell, diradical character, which is inherent to QDMs, may be enhanced due to small HOMO–LUMO energy gap. In this chapter, effects of incorporating QDMs into non-benzenoid aromatic or antiaromatic frameworks are discussed focusing on the open-shell, diradical character with respect to their molecular structures, antiaromaticity, and physical properties related to the open-shell character and molecular orbital levels and materials applications, as well as covering historical works to the current state-of-the-art achievements.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1
Scheme 2
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Scheme 3
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18
Fig. 19
Fig. 20
Fig. 21
Fig. 22
Fig. 23
Fig. 24
Fig. 25
Fig. 26
Fig. 27
Fig. 28
Fig. 29
Fig. 30
Fig. 31
Fig. 32
Scheme 4
Fig. 33
Fig. 34
Fig. 35
Fig. 36
Fig. 37
Fig. 38
Fig. 39
Fig. 40
Fig. 41

Similar content being viewed by others

References

  1. Platz M (1982) In: Borden WT (ed) Diradicals. Wiley, New York, p 195

    Google Scholar 

  2. Flynn CR, Michl J (1974) J Am Chem Soc 96:3280

    Article  CAS  Google Scholar 

  3. Karafiloglou P (1989) J Chem Educ 66:816

    Article  CAS  Google Scholar 

  4. Segura JL, Martín N (1999) Chem Rev 99:3199

    Article  CAS  PubMed  Google Scholar 

  5. Thiele J, Balhorn H (1904) Ber Dtsch Chem Ges 37:1463

    Article  Google Scholar 

  6. Tschitschibabin AE (1907) Ber Dtsch Chem Ges 40:1810

    Article  CAS  Google Scholar 

  7. Waring RK Jr, Sloan GJ (1964) J Chem Phys 40:772

    Article  CAS  Google Scholar 

  8. Montgomery LK, Huffman JC, Jurczak EA, Grendze MP (1986) J Am Chem Soc 108:6004

    Article  CAS  PubMed  Google Scholar 

  9. Abe M (2013) Chem Rev 113:7011

    Article  CAS  PubMed  Google Scholar 

  10. Schmidt R, Brauer H-D (1971) Angew Chem Int Ed 10:506

    Article  CAS  Google Scholar 

  11. Müller E, Pfanz H (1941) Ber Dtsch Chem Ges 74:1051

    Article  Google Scholar 

  12. Schlenk W, Brauns M (1915) Ber Dtsch Chem Ges 48:716

    Article  CAS  Google Scholar 

  13. Dowd P (1972) Acc Chem Res 5:242

    Article  CAS  Google Scholar 

  14. Berson J (1982) In: Borden WT (ed) Diradicals. Wiley, New York, p 151

    Google Scholar 

  15. Iwamura H, Koga N (1993) Acc Chem Res 26:346

    Article  CAS  Google Scholar 

  16. Rajca A (1994) Chem Rev 94:871

    Article  CAS  Google Scholar 

  17. Rajca A (2005) Adv Phys Org Chem 40:153

    CAS  Google Scholar 

  18. Quinkert G, Wiersdorff WW, Finke M, Opitz K (1966) Tetrahedron Lett 7:2193

    Article  Google Scholar 

  19. Quinkert G, Wiersdorf WW, Finke M, Opitz K, von der Haar F-G (1968) Chem Ber 101:2302

    Article  CAS  Google Scholar 

  20. Iwashita S, Ohta E, Higuchi H, Kawai H, Fujiwara K, Ono K, Takenaka M, Suzuki T (2004) Chem Commun 10:2076

    Article  CAS  Google Scholar 

  21. Suzuki T, Sakano Y, Iwai T, Iwashita S, Miura Y, Katoono R, Kawai H, Fujiwara K, Tsuji Y, Fukushima T (2013) Chem Eur J 19:117

    Article  CAS  PubMed  Google Scholar 

  22. Zeng Z, Shi X, Chi C, López Navarrete JT, Casado J, Wu J (2015) Chem Soc Rev 44:6578

    Article  CAS  PubMed  Google Scholar 

  23. Sun Z, Ye Q, Chi C, Wu J (2012) Chem Soc Rev 41:7857

    Article  CAS  PubMed  Google Scholar 

  24. Sun Z, Zeng Z, Wu J (2013) Chem Asian J 8:2894

    Article  CAS  PubMed  Google Scholar 

  25. Sun Z, Wu J (2014) In: Siegel JS, Wu Y-T (eds) Top Curr Chem 349, Polyarenes I. Springer, Heidelberg, p 197

    Google Scholar 

  26. Kubo T (2015) Chem Lett 44:111

    Article  CAS  Google Scholar 

  27. Shimizu A, Nobusue S, Miyoshi H, Tobe Y (2014) Pure Appl Chem 86:517

    Article  CAS  Google Scholar 

  28. Borden WT (1982) In: Borden WT (ed) Diradicals. Wiley, New York, p 1

    Google Scholar 

  29. Lineberger WC, Borden WT (2011) Phys Chem Chem Phys 13:11792

    Article  CAS  PubMed  Google Scholar 

  30. Yamaguchi K (1975) Chem Phys Lett 33:330

    Article  CAS  Google Scholar 

  31. Jung Y, Head-Gordon M (2003) ChemPhysChem 4:522

    Article  CAS  PubMed  Google Scholar 

  32. Snyder JP (ed) (1969) Nonbenzenoid aromatics I. Academic Press, New York

    Google Scholar 

  33. Snyder JP (ed) (1971) Nonbenzenoid aromatics II. Academic Press, New York

    Google Scholar 

  34. Fieser LF, Fieser M (1933) J Am Chem Soc 55:3010

    Article  CAS  Google Scholar 

  35. Binsch G, Tamir I (1969) J Am Chem Soc 91:2450

    Article  CAS  Google Scholar 

  36. Boekelheide V, Vick GK (1956) J Am Chem Soc 78:653

    Article  CAS  Google Scholar 

  37. Boekelheide V, Langeland WE, Liu C-T (1951) J Am Chem Soc 73:2432

    Article  CAS  Google Scholar 

  38. Cava MP, Schlessinger RH (1965) Tetrahedron 21:3051

    Article  CAS  Google Scholar 

  39. Cava MP, Schlessinger RH (1965) Tetrahedron 21:3065

    Article  CAS  Google Scholar 

  40. Cava MP, Schlessinger RH (1965) Tetrahedron 21:3073

    Article  CAS  Google Scholar 

  41. Kolc J, Michl J (1973) J Am Chem Soc 95:7391

    Article  CAS  Google Scholar 

  42. Kawai H, Takeda T, Fujiwara K, Wakeshima M, Hinatsu Y, Suzuki T (2008) Chem Eur J 14:5780

    Article  CAS  PubMed  Google Scholar 

  43. Kolc J, Michl J (1970) J Am Chem Soc 92:4147

    Article  CAS  Google Scholar 

  44. Michl J, Kolc J (1970) J Am Chem Soc 92:4148

    Article  CAS  Google Scholar 

  45. Downing J, Vdořák V, Kolc J, Manzara A, Michl J (1972) Chem Phys Lett 17:70

    Article  CAS  Google Scholar 

  46. Kolc J, Downing JW, Manzara AP, Michl J (1976) J Am Chem Soc 98:930

    Article  CAS  Google Scholar 

  47. Steiner RP, Michl J (1978) J Am Chem Soc 100:6413

    Article  CAS  Google Scholar 

  48. Castellan A, Kolc J, Michl J (1978) J Am Chem Soc 100:6687

    Article  CAS  Google Scholar 

  49. Kertesz M, Choi CH, Yang S (2005) Chem Rev 105:3448

    Article  CAS  PubMed  Google Scholar 

  50. Gellini C, Salvi PR (2010) Symmetry 2:1846

    Article  CAS  Google Scholar 

  51. Hafner K, Häfner KH, König C, Kreuder M, Ploss G, Schluz G, Strum E, Vöpel KH (1963) Angew Chem Int Ed 2:123

    Article  Google Scholar 

  52. Hafner K (1964) Angew Chem Int Ed 52:3165

    Google Scholar 

  53. Hafner K (1982) Pure Appl Chem 54:939

    Article  CAS  Google Scholar 

  54. Hafner K, Krimmer H-P (1980) Angew Chem Int Ed 19:199

    Article  Google Scholar 

  55. Hafner K, Stowasser B, Krimmer H-P, Fischer S, Böhm MC, Lindner HJ (1986) Angew Chem Int Ed 25:630

    Article  Google Scholar 

  56. Dunitz JD, Krüger C, Irngartinger H, Maverick EF, Wang Y, Nixdorf M (1988) Angew Chem Int Ed 27:387

    Article  Google Scholar 

  57. Wang C-C, Tang T-H, Wu L-C, Wang Y (2004) Acta Cryst A60:488

    Article  CAS  Google Scholar 

  58. Klann R, Bäuerle RJ, Laermer F, Elsaesser T, Niemeyer M, Lüttke W (1990) Chem Phys Lett 169:172

    Article  CAS  Google Scholar 

  59. Gellini C, Salvi PR, Hafner K (1993) J Phys Chem 97:8152

    Article  CAS  Google Scholar 

  60. Gellini C, Angeloni L, Salvi PR, Marconi G (1995) J Phys Chem 99:85

    Article  CAS  Google Scholar 

  61. Beer M, Longuet-Higgins HC (1955) J Chem Phys 23:1390

    Article  CAS  Google Scholar 

  62. Rentzepis PM (1969) Chem Phys Lett 3:717

    Article  CAS  Google Scholar 

  63. Murata S, Iwanaga C, Toda T, Kokubun H (1972) Chem Phys Lett 15:152

    Article  Google Scholar 

  64. Bearpark MJ, Celani P, Jolibois F, Olivucci M, Robb MA, Bernardi F (1999) Mol Phys 96:645

    Article  CAS  Google Scholar 

  65. Arnold BR, Michl J (1990) In: Platz MS (ed) Kinetics and spectroscopy of carbenes and biradicals. Plenum Press, New York, p 1

    Google Scholar 

  66. Whitman DW, Carpenter BK (1980) J Am Chem Soc 102:4272

    Article  CAS  Google Scholar 

  67. Whitman DW, Carpenter BK (1982) J Am Chem Soc 104:6473

    Article  CAS  Google Scholar 

  68. Carpenter BK (1983) J Am Chem Soc 105:1700

    Article  CAS  Google Scholar 

  69. Kozuch S (2014) RSC Adv 4:21650

    Article  CAS  Google Scholar 

  70. Nakajima T, Saijo T, Yamaguchi H (1964) Tetrahedron 20:2119

    Article  CAS  Google Scholar 

  71. Hafner K, Stowasser B, Krimmer H-P, Fischer S, Böhm MC, Lindner HJ (1963) Angew Chem Int Ed 2:123

    Article  Google Scholar 

  72. Gellini C, Cardini G, Salvi PR, Marconi G, Hafner K (1993) J Phys Chem 97:1286

    Article  CAS  Google Scholar 

  73. Heilbronner E, Yang Z-Z (1987) Angew Chem Int Ed 26:360

    Article  Google Scholar 

  74. Hertwig RH, Holthausen MC, Koch W, Maksić ZB (1994) Angew Chem Int Ed 33:1192

    Article  Google Scholar 

  75. Hertwig RH, Holthausen MC, Koch W, Maksić ZB (1995) Int J Quantum Chem 54:147

    Article  CAS  Google Scholar 

  76. Nendel M, Goldfuss B, Houk KN, Hafner K (1999) J Mol Struct 461–462:23

    Article  Google Scholar 

  77. Nendel M, Goldfuss B, Beno B, Houk KN, Hafner K, Lindner HJ (1999) Pure Appl Chem 71:221

    Article  CAS  Google Scholar 

  78. Moroni L, Gellini C, Salvi PR (2004) J Mol Struct 667:1

    Article  CAS  Google Scholar 

  79. Makino M, Aihara J (2008) Phys Chem Chem Phys 10:591

    Article  CAS  PubMed  Google Scholar 

  80. Julg A, François P (1967) Theo Chim Acta 8:249

    Article  CAS  Google Scholar 

  81. Jartín RS, Ligabue A, Soncini A, Lazzeretti P (2002) J Phys Chem A 106:11806

    Article  CAS  Google Scholar 

  82. Havenith RWA, Engelberts JJ, Fowler PW, Steiner E, van Lenthe JH, Lazzeretti P (2004) Phys Chem Phys Chem 6:289

    Article  CAS  Google Scholar 

  83. Motomura S, Nakano M, Fukui H, Yoneda K, Kubo T, Carion R, Champagne B (2011) Phys Chem Chem Phys 13:20575

    Article  CAS  PubMed  Google Scholar 

  84. Prinzbach H, Knothe L (1986) Pure Appl Chem 58:25

    Article  CAS  Google Scholar 

  85. Wiersum UE, Jenneskens LW (1993) Tetrahedron Lett 34:6615

    Article  CAS  Google Scholar 

  86. Nakajima T (1971) Pure Appl Chem 28:219

    Article  CAS  Google Scholar 

  87. Hess BA Jr, Shaad LJ (1971) J Org Chem 36:3418

    Article  CAS  Google Scholar 

  88. Toyota A (1975) Bull Chem Soc Jpn 48:1152

    Article  CAS  Google Scholar 

  89. Böhm MC, Schütt J (1992) J Phys Chem 96:3674

    Article  Google Scholar 

  90. Randić M (2003) Chem Rev 103:3449

    Article  CAS  PubMed  Google Scholar 

  91. Tobe Y (2015) Chem Rec 15:86

    Article  CAS  PubMed  Google Scholar 

  92. Prinzbach H, Babsch H, Hunkler D (1978) Tetrahedron Lett 19:649

    Article  Google Scholar 

  93. Prinzbach H, Bingmann H, Beck A, Hunkler D, Sauter H, Hädicke E (1981) Chem Ber 114:1697

    Article  CAS  Google Scholar 

  94. Prinzbach H, Schneider H-W (1973) Angew Chem Int Ed 12:1007

    Article  Google Scholar 

  95. Prinzbach H, Knothe L, Schneider H-W (1973) Angew Chem Int Ed 12:1009

    Article  Google Scholar 

  96. Kuroda S, Asao T, Funamizu M, Kurihara H, Kitahara Y (1976) Tetrahedron Lett 17:251

    Article  Google Scholar 

  97. Beck A, Bingmann H, Kagabu S, Knothe L, Hädicke E, Prinzbach H (1983) Chem Ber 116:1963

    Article  CAS  Google Scholar 

  98. Kubo T (2015) Chem Rec 15:218

    Article  CAS  PubMed  Google Scholar 

  99. Motita Y, Nishida S (2010) In: Hicks R (ed) Stable radicals. Wiley, Chichester, p 81

    Google Scholar 

  100. Goto K, Kubo T, Yamamoto K, Nakasuji K, Sato K, Shiomi D, Takui T, Kubota M, Kobayashi T, Yakusi K, Ouyang J (1999) J Am Chem Soc 121:1619

    Article  CAS  Google Scholar 

  101. Kubo T, Shimizu A, Sakamoto M, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Morita Y, Nakasuji K (2005) Angew Chem Int Ed 44:6564

    Article  CAS  Google Scholar 

  102. Kubo T, Shimizu A, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Morita Y, Nakasuji K (2007) Org Lett 9:81

    Article  CAS  PubMed  Google Scholar 

  103. Shimizu A, Hirao Y, Matsumoto K, Kurata H, Kubo T, Uruichi M, Yakushi K (2012) Chem Commun 48:5629

    Article  CAS  Google Scholar 

  104. Shimizu A, Uruichi M, Yakushi K, Matsuzaki H, Okamoto H, Nakano M, Hirao Y, Matsumoto K, Kurata H, Kubo T (2009) Angew Chem Int Ed 48:5482

    Article  CAS  Google Scholar 

  105. Shimizu A, Kubo T, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Hirao Y, Matsumoto K, Kurata H, Morita Y, Nakasuji K (2010) J Am Chem Soc 132:14421

    Article  CAS  PubMed  Google Scholar 

  106. Chikamatsu M, Mikami T, Chisaka J, Yoshida Y, Azumi R, Yase K, Shimizu A, Kubo T, Morita Y, Nakasuji K (2007) App Phys Lett 91:043506

    Article  CAS  Google Scholar 

  107. Mou Z, Uchida K, Kubo T, Kertesz M (2014) J Am Chem Soc 136:18009

    Article  CAS  PubMed  Google Scholar 

  108. Uchida K, Mou Z, Kertesz M, Kubo T (2016) J Am Chem Soc 138:4665

    Article  CAS  PubMed  Google Scholar 

  109. Nakano M, Kishi R, Nitta T, Kubo T, Nakasuji K, Kamada K, Ohta K, Champagne B, Botek E, Yamaguchi K (2005) J Phys Chem A 109:885

    Article  CAS  PubMed  Google Scholar 

  110. Ohta S, Nakano M, Kubo T, Kamada K, Ohta K, Kishi R, Nakagawa N, Champagne B, Botek E, Umezaki S-Y, Takebe A, Takahashi H, Furukawa S-I, Morita Y, Nakasuji K, Yamaguchi K (2006) Chem Phys Lett 420:432

    Article  CAS  Google Scholar 

  111. Nakano M, Kubo T, Kamada K, Ohta K, Kishi R, Ohta S, Nakagawa N, Takahashi H, Furukawa S-I, Morita Y, Nakasuji K, Yamaguchi K (2006) Chem Phys Lett 418:142

    Article  CAS  Google Scholar 

  112. Kamada K, Ohta K, Kubo T, Shimizu A, Morita Y, Nakasuji K, Kishi R, Ohta S, Furukawa S-I, Takahashi H, Nakano M (2007) Angew Chem Int Ed 46:3544

    Article  CAS  Google Scholar 

  113. Kamada K, Ohta K, Shimizu A, Kubo T, Kishi R, Takahashi H, Botek E, Champagne B, Nakano M (2010) J Phys Chem Lett 1:937

    Article  CAS  Google Scholar 

  114. Frederickson CK, Rose BD, Haley MM (2017) Acc Chem Res 50:977

    Article  CAS  PubMed  Google Scholar 

  115. Fix AG, Chase DT, Haley MM (2014) In: Siegel JS, Wu Y-T (eds) Polyarenes I, Top Curr Chem 349:159

  116. Haley MM (2015) Chem Rec 15:1140

    Article  CAS  PubMed  Google Scholar 

  117. Zhou Q, Carroll PJ, Swager TM (1994) J Org Chem 59:1294

    Article  CAS  Google Scholar 

  118. Scherf U (1993) Macromol Rapid Commun 14:575

    Article  CAS  Google Scholar 

  119. Chase DT, Rose BD, McClintock SP, Zakharov LN, Haley MM (2011) Angew Chem Int Ed 50:1127

    Article  CAS  Google Scholar 

  120. Chase DT, Fix AG, Kang SJ, Rose BD, Weber CD, Zhong Y, Zakharov LN, Lonergan MC, Nuckolls C, Haley MM (2012) J Am Chem Soc 134:10349

    Article  CAS  PubMed  Google Scholar 

  121. Rose BD, Zakharov LN, Haley MM (2013) Acta Cryst E69:o890

    Google Scholar 

  122. Chase DT, Fix AG, Rose BD, Weber CD, Nobusue S, Stockwell CE, Zakharov LN, Lonergan MC, Haley MM (2011) Angew Chem Int Ed 50:11103

    Article  CAS  Google Scholar 

  123. Fu X, Zhao D (2015) Org Lett 17:5694

    Article  CAS  PubMed  Google Scholar 

  124. Nishida J-I, Tsukaguchi S, Yamashita Y (2012) Chem Eur J 18:8964

    Article  CAS  PubMed  Google Scholar 

  125. Frederickson CK, Zakharov LN, Haley MM (2016) J Am Chem Soc 138:16827

    Article  CAS  PubMed  Google Scholar 

  126. Young BS, Chase DT, Marshall JL, Vonnegut CL, Zakharov LN, Haley MM (2014) Chem Sci 5:1008

    Article  CAS  PubMed  Google Scholar 

  127. Marshall JL, Uchida K, Frederickson CK, Schütt C, Zeidell AM, Goetz KP, Finn TW, Jarolimek K, Zakharov LN, Risko C, Heges R, Jurchescu OD, Haley MM (2016) Chem Sci 7:5547

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  128. Marshall JL, O’Neal NJ, Zakharov LN, Haley MM (2016) J Org Chem 81:3674

    Article  CAS  PubMed  Google Scholar 

  129. Ren L, Liu C, Wang Z, Zhu X (2016) J Mater Chem C 4:5202

    Article  CAS  Google Scholar 

  130. Gershoni-Poranne R, Stanger A (2014) Chem Eur J 20:5673

    Article  CAS  PubMed  Google Scholar 

  131. Anthony JE, Brooks JS, Eaton DL, Parkin SR (2001) J Am Chem Soc 123:9482

    Article  CAS  PubMed  Google Scholar 

  132. Ryno SM, Risko C, Bredas J-L (2014) J Am Chem Soc 136:6421

    Article  CAS  PubMed  Google Scholar 

  133. Lim Y-F, Shu Y, Parkin SR, Anthony JE, Malliars GG (2009) J Mater Chem 19:3049

    Article  CAS  Google Scholar 

  134. Rose BD, Summer NJ, Filatov AS, Peters SJ, Zakharov LN, Petrukhina MA, Haley MM (2014) J Am Chem Soc 136:9181

    Article  CAS  PubMed  Google Scholar 

  135. Barker JE, Frederickson CK, Jones MH, Zakharov LN, Haley MM (2017) Org Lett 19:5312

    Article  CAS  PubMed  Google Scholar 

  136. Rudebush GE, Zafra JL, Jorner K, Fukuda K, Marshall JL, Arrechea-Marcos I, Espejo GL, Ortiz RP, Gómes-García CJ, Zakharov LN, Nakano M, Ottosson H, Casado J, Haley MM (2016) Nat Chem 8:753

    Article  CAS  Google Scholar 

  137. Rose BD, Vonnegut CL, Zakharov LN, Haley MM (2012) Org Lett 14:2426

    Article  CAS  PubMed  Google Scholar 

  138. Rudebush GE, Espejo GL, Zafra JL, Peña-Alvarez M, Spisak SN, Fukuda K, Wei Z, Nakano M, Petrukhina M, Casado J, Haley MM (2016) J Am Chem Soc 138:12648

    Article  CAS  Google Scholar 

  139. Maekawa T, Ueno H, Segawa Y, Haley MM, Itami K (2016) Chem Sci 7:650

    Article  CAS  PubMed  Google Scholar 

  140. Hu P, Lee S, Herng TS, Aratani N, Gonçalves TP, Qi Q, Shi X, Yamada H, Huang K-W, Ding J, Kim D, Wu J (2016) J Am Chem Soc 138:1065

    Article  CAS  PubMed  Google Scholar 

  141. Yang X, Liu D, Miao Q (2014) Angew Chem Int Ed 53:6786

    Article  CAS  Google Scholar 

  142. Yang X, Shi X, Aratani N, Gonçalves TP, Huang K-W, Yamada H, Chi C, Miao Q (2016) Chem Sci 7:6176

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  143. Hibi D, Kitabayashi K, Fujita K, Takeda T, Tobe Y (2016) J Org Chem 81:3735

    Article  CAS  PubMed  Google Scholar 

  144. Liu J, Ma J, Zhang K, Ravat P, Machata P, Avdoshenko S, Hennersdorf F, Komber H, Pisula W, Weigand JJ, Popov AA, Berger R, Müllen K, Feng X (2017) J Am Chem Soc 139:7513

    Article  CAS  PubMed  Google Scholar 

  145. Fix AG, Deal PE, Vonnegut CL, Rose BD, Zakharov LN, Haley MM (2013) Org Lett 15:1362

    Article  CAS  PubMed  Google Scholar 

  146. Sbargoud K, Mamada M, Marrot J, Tokito S, Yassar A, Frigoli M (2015) Chem Sci 6:3402

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  147. Étienne A, Le Berre A (1956) C R Hebd Seances Acad Sci 242:1493

    Google Scholar 

  148. Étienne A, Le Berre A (1956) C R Hebd Seances Acad Sci 242:1899

    Google Scholar 

  149. Le Berre A (1956) C R Hebd Seances Acad Sci 242:2365

    Google Scholar 

  150. Le Berre A (1957) Ann Chim 13:371

    Google Scholar 

  151. Chalvet O, Peltier J (1956) Bull Soc Chim Fr 1667

  152. Shimizu A, Tobe Y (2011) Angew Chem Int Ed 50:6906

    Article  CAS  Google Scholar 

  153. Fukuda K, Nagami T, Fujiyoshi JY, Nakano M (2015) J Phys Chem A 119:10620

    Article  CAS  PubMed  Google Scholar 

  154. Gisin M, Wirz J (1976) Helv Chim Acta 59:2273

    Article  CAS  Google Scholar 

  155. Steiner RP, Miller RD, Dewey HL, Michl J (1979) J Am Chem Soc 101:1820

    Article  CAS  Google Scholar 

  156. Cofino WP, Engelsma M, Kamminga DA, Hoornweg PG, Gooijer C, MacLean C, Velthost NH (1984) Spectrochim Acta 40A:269

    Article  CAS  Google Scholar 

  157. Jones WD, Pomfret A, Eife RL (1983) J Chem Soc Perkin Trans 1459

  158. Miyoshi H, Nobusue S, Shimizu A, Hisaki I, Miyata M, Tobe T (2014) Chem Sci 5:163

    Article  CAS  Google Scholar 

  159. Nobusue S, Tobe Y (2016) Synlett 21:2140

    Google Scholar 

  160. Shimizu A, Kishi R, Nakano M, Shiomi D, Sato K, Takui T, Hisaki I, Miyata M, Tobe Y (2013) Angew Chem Int Ed 52:6076

    Article  CAS  Google Scholar 

  161. Miyoshi H, Miki M, Hirano S, Shimizu A, Kishi R, Fukuda K, Shiomi D, Sato K, Takui T, Hisaki I, Nakano M, Tobe Y (2017) J Org Chem 82:1380

    Article  CAS  PubMed  Google Scholar 

  162. Dreeler JJ, Zhou Z, Marshall JL, Kishi R, Takamuku S, Wei Z, Spisak SN, Nakano M, Petrukhina MA, Haley MM (2017) Angew Chem Int Ed 56:15363

    Article  CAS  Google Scholar 

  163. Baird NC (1972) J Am Chem Soc 94:4941

    Article  CAS  Google Scholar 

  164. Hellwinkel D, Reiff G (1970) Angew Chem Int Ed 82:516

    Article  Google Scholar 

  165. Nobusue S, Miyoshi H, Shimizu A, Hisaki I, Fukuda K, Nakano M, Tobe Y (2015) Angew Chem Int Ed 54:2090

    Article  CAS  Google Scholar 

  166. Miyoshi H, Nobusue S, Shimizu A, Tobe Y (2015) Chem Soc Rev 44:6560

    Article  CAS  PubMed  Google Scholar 

  167. Aihara J (2016) Bull Chem Soc Jpn 89:1425

    Article  CAS  Google Scholar 

  168. Baryshnikov GV, Valiev RR, Karaush NN, Sundholm D, Minaev BF (2016) Phys Chem Chem Phys 18:8980

    Article  CAS  PubMed  Google Scholar 

  169. Dickens TK, Mallion RB (2013) Phys Chem Chem Phys 15:8245

    Article  CAS  PubMed  Google Scholar 

  170. Miyoshi H, Nishinaga T, Hisaki I, Nakano M, Petrukhina M, Tobe Y unpublished results

  171. Das S, Herng TS, Zafra JL, Burrezo PM, Kitano M, Ishida M, Gopalakrishna TY, Hu P, Osaka A, Casado J, Ding J, Casanova D, Wu J (2016) J Am Chem Soc 138:7782

    Article  CAS  PubMed  Google Scholar 

  172. Lu X, Lee S, Hong Y, Phan H, Gopalakrishna TY, Herng TS, Tanaka T, Sandoval-Salinas ME, Zeng W, Ding J, Casanova D, Osuka A, Kim D, Wu J (2017) J Am Chem Soc 139:13173

    Article  CAS  PubMed  Google Scholar 

  173. Lu X, Lee S, Kim JO, Gopalakrishna TY, Phan H, Herng TS, Lim Z, Zeng Z, Ding J, Kim D, Wu J (2016) J Am Chem Soc 138:13048

    Article  CAS  PubMed  Google Scholar 

  174. Trost BM, Kinson PL (1975) J Am Chem Soc 97:2438

    Article  CAS  Google Scholar 

  175. Reid DH, Stafford WH, Ward JP (1955) J Chem Soc 1193

  176. Zahradník R, Michl J, Pancíř J (1966) Tetrahedron 22:1355

    Article  Google Scholar 

  177. Hess BA Jr, Schaad LJ (1971) J Org Chem 36:3418

    Article  CAS  Google Scholar 

  178. DasGupta A, DasGupta NK (1974) Theoret Chim Acta 33:177

    Article  CAS  Google Scholar 

  179. Baumgartner P, Weltin E, Wagnière G, Heilbronner E (1965) Helv Chim Acta 48:751

    Article  CAS  Google Scholar 

  180. Nendel M, Goldfuss B, Houk KN, Hafner K, Grieser U (1999) Theor Chem Acta 102:397

    Article  CAS  Google Scholar 

  181. Grieser U, Hafner K (1994) Chem Ber 127:2307

    Article  CAS  Google Scholar 

  182. Das S, Wu J (2015) Org Lett 17:5854

    Article  CAS  PubMed  Google Scholar 

  183. Brand K (1912) Ber Dtsch Chem Ges 45:3071

    Article  Google Scholar 

  184. Bergmann ED (1959) In: Ginsburg D (ed) Non-Benzenoid Aromatic Compounds. Interscience, New York, p 141

    Google Scholar 

  185. Parkhurst RR, Swager TM (2014) In: Siegel JS, Wu YT (eds) Polyarenes II. Springer, Heidelberg, p 141

    Google Scholar 

  186. Rudebusch GE, Haley MM (2016) In: Miao Q (ed) Polycyclic Arenes and Heteroarenes. Wiley, Weinheim, p 37

    Google Scholar 

  187. Konishi A, Okada Y, Nakano M, Sugisaki K, Sato K, Kakui T, Yasuda M (2017) J Am Chem Soc 139:15284

    Article  CAS  PubMed  Google Scholar 

  188. Wang Q, Gopalakrishna TY, Phan H, Herng TS, Dong S, Ding J, Chi C (2017) Angew Chem Int Ed 56:11415

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The author is grateful to for continued support by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology.

Author information

Authors and Affiliations

  1. The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka, 567-0047, Japan

    Yoshito Tobe

Authors
  1. Yoshito Tobe
    View author publications

    You can also search for this author inPubMed Google Scholar

Corresponding author

Correspondence to Yoshito Tobe.

Additional information

This article is part of the Topical Collection “Physical Organic Chemistry of Quinodimethanes”; edited by Yoshito Tobe, Takashi Kubo.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tobe, Y. Quinodimethanes Incorporated in Non-Benzenoid Aromatic or Antiaromatic Frameworks. Top Curr Chem (Z) 376, 12 (2018). https://doi.org/10.1007/s41061-018-0189-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-018-0189-0

Keywords