Synthesis 2019; 51(24): 4576-4581
DOI: 10.1055/s-0039-1690206
paper
© Georg Thieme Verlag Stuttgart · New York

Sumanene Hexaester: An Electron-Deficient Buckybowl

Hideaki Toda
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   eMail: hsakurai@chem.eng.osaka-u.ac.jp
,
Yuta Uetake
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   eMail: hsakurai@chem.eng.osaka-u.ac.jp
,
Yumi Yakiyama
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   eMail: hsakurai@chem.eng.osaka-u.ac.jp
,
Hironobu Nakazawa
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   eMail: hsakurai@chem.eng.osaka-u.ac.jp
,
Takashi Kajitani
b   Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
,
Takanori Fukushima
b   Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
,
Hidehiro Sakurai
a   Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan   eMail: hsakurai@chem.eng.osaka-u.ac.jp
› Institutsangaben
This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas ‘π-Figuration’ (no. 26102002 for H.S. and no. 26102008 for T.F.) and ‘Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials’ from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Weitere Informationen

Publikationsverlauf

Received: 19. August 2019

Accepted after revision: 12. September 2019

Publikationsdatum:
30. September 2019 (online)


Abstract

2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexa­substituted sumanene with CO2Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation­ using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.

Supporting Information

 
  • References


    • Selected reviews on PAHs:
    • 1a Scott LT, Bronstein HE, Preda DV, Ansems RB. M, Bratcher MS, Hagen S. Pure Appl. Chem. 1999; 71: 209
    • 1b Watson MD, Fechtenkötter A, Müllen K. Chem. Rev. 2001; 101: 1267
    • 1c Tsefrikas VM, Scott LT. Chem. Rev. 2006; 106: 4868
    • 1d Wu J, Pisula W, Müllen K. Chem. Rev. 2007; 107: 718
    • 1e Sygula A. Eur. J. Org. Chem. 2011; 1611
    • 1f Chen L, Hernandez Y, Feng X, Müllen K. Angew. Chem. Int. Ed. 2012; 51: 7640
    • 1g Sun Z, Ye Q, Chi C, Wu J. Chem. Soc. Rev. 2012; 41: 7857
    • 1h Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
    • 1i Segawa Y, Ito H, Itami K. Nat. Rev. Mater. 2016; 1: 15002
    • 2a Rohr U, Schlichting P, Böhm A, Gross M, Meerholz K, Bräuchle C, Müllen K. Angew. Chem. Int. Ed. 1998; 37: 1434
    • 2b Langhals H, Kirner S. Eur. J. Org. Chem. 2000; 365
    • 2c Hirayama S, Sakai H, Araki Y, Tanaka M, Imakawa M, Wada T, Takenobu T, Hasobe T. Chem. Eur. J. 2014; 20: 9081
    • 2d Vollbrecht J, Bock H, Wiebeler C, Schumacher S, Kitzerow H. Chem. Eur. J. 2014; 20: 12026
    • 2e Vollbrecht J, Wiebeler C, Neuba A, Bock H, Schumacher S, Kitzerow H. J. Phys. Chem. C 2016; 120: 7839
    • 2f Vollbrecht J, Blazy S, Dierks P, Peurifoy S, Bock H, Kitzerow H. ChemPhysChem 2017; 18: 2024
    • 3a Hassheider T, Benning SA, Kitzerow H.-S, Achard M.-F, Bock H. Angew. Chem. Int. Ed. 2001; 40: 2060
    • 3b Bock H, Rajaoarivelo M, Clavaguera S, Grelet É. Eur. J. Org. Chem. 2006; 2889
    • 3c Grelet É, Bock H. Europhys. Lett. 2006; 73: 712
    • 3d Saïdi-Besbes S, Grelet É, Bock H. Angew. Chem. Int. Ed. 2006; 45: 1783
    • 3e Alibert-Fouet A, Seguy I, Bobo J.-F, Destruel P, Bock H. Chem. Eur. J. 2007; 13: 1746
    • 3f Grelet E, Dardel S, Bock H, Goldmann M, Lacaze E, Nallet F. Eur. Phys. J. E 2010; 31: 343
    • 3g Osawa T, Kajitani T, Hashizume D, Ohsumi H, Sasaki S, Takata M, Koizumi Y, Saeki A, Seki S, Fukushima T, Aida T. Angew. Chem. Int. Ed. 2012; 51: 7990
    • 3h Ferreira M, Moreira TS, Cristiano R, Gallardo H, Bentaleb A, Dechambenoit P, Hillard EA, Durola F, Bock H. Chem. Eur. J. 2018; 24: 2214

      Selected reviews on buckybowls:
    • 4a Scott LT. Pure Appl. Chem. 1996; 68: 291
    • 4b Wu Y.-T, Siegel JS. Chem. Rev. 2006; 106: 4843
    • 4c Amaya T, Hirao T. Chem. Commun. 2011; 47: 10524
    • 4d Higashibayashi S, Sakurai H. Chem. Lett. 2011; 40: 122
    • 4e Schmidt BM, Lentz D. Chem. Lett. 2014; 43: 171
    • 4f Saito M, Shinokubo H, Sakurai H. Mater. Chem. Front. 2018; 2: 635
    • 5a Imamura K, Takimiya K, Aso Y, Otsubo T. Chem. Commun. 1999; 1859
    • 5b Furukawa S, Kobayashi J, Kawashima T. J. Am. Chem. Soc. 2009; 131: 14192
    • 5c Saito M, Tanikawa T, Tajima T, Guo JD, Nagase S. Tetrahedron Lett. 2010; 51: 672
    • 5d Furukawa S, Kobayashi J, Kawashima T. Dalton Trans. 2010; 39: 9329
    • 5e Tanikawa T, Saito M, Guo JD, Nagase S. Org. Biomol. Chem. 2011; 9: 1731
    • 5f Tan Q, Higashibayashi S, Karanjit S, Sakurai H. Nat. Commun. 2012; 3: 891
    • 5g Tanikawa T, Saito M, Guo JD, Nagase S, Minoura M. Eur. J. Org. Chem. 2012; 7135
    • 5h Li X, Zhu Y, Shao J, Wang B, Zhang S, Shao Y, Jin X, Yao X, Fang R, Shao X. Angew. Chem. Int. Ed. 2014; 53: 535
    • 5i Ito S, Tokimatsu Y, Nozaki K. Angew. Chem. Int. Ed. 2015; 54: 7256
    • 5j Yokoi H, Hiraoka Y, Hiroto S, Sakamaki D, Seki S, Shinokubo H. Nat. Commun. 2015; 6: 8215
    • 5k Wang S, Li X, Hou X, Sun Y, Shao X. Chem. Commun. 2016; 52: 14486
    • 5l Hou X, Zhu Y, Qin Y, Chen L, Li X, Zhang H.-L, Xu W, Zhu D, Shao X. Chem. Commun. 2017; 53: 1546
    • 5m Furukawa S, Suda Y, Kobayashi J, Kawashima T, Tada T, Fujii S, Kiguchi M, Saito M. J. Am. Chem. Soc. 2017; 139: 5787
    • 5n Kaewmati P, Tan Q, Higashibayashi S, Yakiyama Y, Sakurai H. Chem. Lett. 2017; 46: 146
    • 5o Tan Q, Zhou D, Zhang T, Liu B, Xu B. Chem. Commun. 2017; 53: 10279
    • 5p Tan Q, Kaewmati P, Higashibayashi S, Kawano M, Yakiyama Y, Sakurai H. Bull. Chem. Soc. Jpn. 2018; 91: 531
    • 5q Wang S, Yan C, Shang J, Wang W, Yuan C, Zhang H.-L, Shao X. Angew. Chem. Int. Ed. 2019; 58: 3819
    • 6a Seiders TJ, Elliott EL, Grube GH, Siegel JS. J. Am. Chem. Soc. 1999; 121: 7804
    • 6b Sygula A, Rabideau PW. J. Am. Chem. Soc. 2000; 122: 6323
    • 6c Xu G, Sygula A, Marcinow Z, Rabideau PW. Tetrahedron Lett. 2000; 41: 9931
    • 6d Grube GH, Elliott EL, Steffens RJ, Jones CS, Baldridge KK, Siegel JS. Org. Lett. 2003; 5: 713
    • 6e Wu Y.-T, Bandera D, Maag R, Linden A, Baldridge KK, Siegel JS. J. Am. Chem. Soc. 2008; 130: 10729
    • 6f Baldridge KK, Hardcastle KI, Seiders TJ, Siegel JS. Org. Biomol. Chem. 2010; 8: 53
    • 6g Pogoreltsev A, Solel E, Pappo D, Keinan E. Chem. Commun. 2012; 48: 5425

      Functionalization at benzylic carbons:
    • 7a Sakurai H, Daiko T, Hirao T. Science 2003; 301: 1878
    • 7b Sakurai H, Daiko T, Sakane H, Amaya T, Hirao T. J. Am. Chem. Soc. 2005; 127: 11580
    • 7c Amaya T, Nakata T, Hirao T. J. Am. Chem. Soc. 2009; 131: 10810
    • 7d Amaya T, Hifumi M, Okada M, Shimizu Y, Moriuchi T, Segawa K, Ando Y, Hirao T. J. Org. Chem. 2011; 76: 8049
    • 7e Amaya T, Mori K, Wu H.-L, Ishida S, Nakamura J, Murata K, Hirao T. Chem. Commun. 2007; 1902
    • 7f Higashibayashi S, Nasir Baig RB, Morita Y, Sakurai H. Chem. Lett. 2012; 41: 84
    • 7g Higashibayashi S, Tsuruoka R, Soujanya Y, Purushotham U, Sastry GN, Seki S, Ishikawa T, Toyota S, Sakurai H. Bull. Chem. Soc. Jpn. 2012; 85: 450
    • 7h Schmidt BM, Topolinski B, Higashibayashi S, Kojima T, Kawano M, Lentz D, Sakurai H. Chem. Eur. J. 2013; 19: 3282
    • 7i Higashibayashi S, Onogi S, Srivastava HK, Sastry GN, Wu Y.-T, Sakurai H. Angew. Chem. Int. Ed. 2013; 52: 7314
    • 7j Amaya T, Ito T, Hirao T. Eur. J. Org. Chem. 2014; 3531
    • 7k Amaya T, Ito T, Katoh S, Hirao T. Tetrahedron 2015; 71: 5906
    • 7l Yakiyama Y, Wang Y, Hatano S, Abe M, Sakurai H. Chem. Asian J. 2019; 14: 1844

      Functionalization at aromatic carbons:
    • 8a Shrestha BB, Karanjit S, Panda G, Higashibayashi S, Sakurai H. Chem. Lett. 2013; 42: 386
    • 8b Amaya T, Kobayashi K, Hirao T. Asian J. Org. Chem. 2013; 2: 642
    • 8c Shrestha BB, Higashibayashi S, Sakurai H. Beilstein J. Org. Chem. 2014; 10: 841
    • 8d Shrestha BB, Karanjit S, Higashibayashi S, Amaya T, Hirao T, Sakurai H. Asian J. Org. Chem. 2015; 4: 62
    • 8e Ngamsomprasert N, Panda G, Higashibayashi S, Sakurai H. J. Org. Chem. 2016; 81: 11978
    • 8f Ngamsomprasert N, Yakiyama Y, Sakurai H. Chem. Lett. 2017; 46: 446
    • 8g Toda H, Yakiyama Y, Shoji Y, Ishiwari F, Fukushima T, Sakurai H. Chem. Lett. 2017; 46: 1368
    • 8h Shoji Y, Kajitani T, Ishiwari F, Ding Q, Sato H, Anetai H, Akutagawa T, Sakurai H, Fukushima T. Chem. Sci. 2017; 8: 8405
    • 8i Hisaki I, Toda H, Sato H, Tohnai N, Sakurai H. Angew. Chem. Int. Ed. 2017; 56: 15294
    • 9a Ueda T, Konishi H, Manabe K. Org. Lett. 2012; 14: 3100
    • 9b Fujihara T, Hosoki T, Katafuchi Y, Iwai T, Terao J, Tsuji Y. Chem. Commun. 2012; 48: 8012
  • 10 Mebs S, Weber M, Luger P, Schmidt BM, Sakurai H, Higashibayashi S, Onogi S, Lentz D. Org. Biomol. Chem. 2012; 10: 2218
  • 11 Armaković S, Armaković SJ, Šetrajčić JP, Šetrajčić IJ. Chem. Phys. Lett. 2013; 578: 156
  • 12 DFT/TD-DFT calculations of 5 for assignment of the transitions corresponding to UV absorption bands did not converge, probably due to the flexibility of the phenoxycarbonyl groups.
  • 13 Zanello P, Fedi S, Fabrizi de Biani F, Giorgi G, Amaya T, Sakane H, Hirao T. Dalton Trans. 2009; 9192