Synthesis
DOI: 10.1055/s-0040-1707177
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Peripherally Arylated Tetrathiafulvalenes Extended with an Anthraquinoid Spacer via Pd-Catalyzed C–H Arylation and Construction of a Double-Helical Cobalt-Based Metal-Organic Framework

a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
b  Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan
,
Keisuke Henmi
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
,
Hitoshi Kimura
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
,
Ryo Sakakibara
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
,
c  Faculty of Science and Technology, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan
,
Takashi Shirahata
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
b  Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan
d  Research Unit for Development of Organic Superconductors, Ehime University, Matsuyama, Ehime 790-8577, Japan
,
e  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
,
Yohji Misaki
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan   Email: misaki.yohji.mx@ehime-u.ac.jp
b  Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan
d  Research Unit for Development of Organic Superconductors, Ehime University, Matsuyama, Ehime 790-8577, Japan
› Author Affiliations
This work was partially supported by JPSP KAKENHI Grant Number JP26410095, and by MEXT KAKENHI Grant Numbers JP15H03798 and 19H02690. This work was also supported by Grant-in-Aid for Research Promotion, Ehime University, to The Research Unit for Development of Organic Superconductors and to The Research Unit for Power Generation and Storage Materials.
Further Information

Publication History

Received: 15 May 2020

Accepted after revision: 10 June 2020

Publication Date:
13 July 2020 (online)


Published as part of the Special Topic Functional Organic Molecules

Abstract

Peripherally arylated tetrathiafulvalenes with an anthraquinoid spacer (TTFAQs) have been synthesized by using palladium-catalyzed direct C–H arylation of the 1,3-dithiole rings. Electrochemical analysis by cyclic voltammetry has revealed that the new tetraarylated TTFAQs show one pair of simultaneous two-electron transfer waves as the parent TTFAQ does. The hydrolysis of the tetra(p-ethoxycarbonylphenyl)-substituted derivative affords the corresponding tetracarboxylic acid, which forms a new double-helical metal-organic framework upon complexation with cobalt(III) nitrate.

Supporting Information

 
  • References

  • 1 TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene. Yamada J, Sugimoto T. Kodansha-Springer; Tokyo: 2004

    • For reviews on the TTF materials, see:
    • 2a Canevet D, Sallé M, Zhang G, Zhang D, Zhu D. Chem. Commun. 2009; 2245
    • 2b Gorgues A, Hudhomme P, Sallé M. Chem. Rev. 2004; 104: 5151
    • 2c Segura JL, Martín N. Angew. Chem. Int. Ed. 2001; 40: 1372
    • 2d Iyoda M, Hasegawa M, Miyake Y. Chem. Rev. 2004; 104: 5085
    • 2e Lorcy D, Bellec N, Fourmigué M, Avarvari N. Coord. Chem. Rev. 2009; 253: 1398
    • 2f Bergkamp JJ, Decurtins S, Liu S.-X. Chem. Soc. Rev. 2015; 44: 863
    • 2g Pop F, Avarvari N. Chem. Commun. 2016; 52: 7906
    • 2h Hasegawa M, Iyoda M. In Organic Redox Systems . Nishinaga T. Wiley; Hoboken: 2016. Chap. 4, 89
  • 3 Application to molecular conductors: Misaki Y. Sci. Technol. Adv. Mater. 2009; 10: 024301

    • Application to positive electrode materials for rechargeable batteries:
    • 4a Inatomi Y, Hojo N, Yamamoto T, Shimada M, Watanabe S. 213th ECS Meeting, Phoenix. 2008; DOI: Abstract 167.
    • 4b Inatomi Y, Hojo N, Yamamoto T, Watanabe S, Misaki Y. ChemPlusChem 2012; 77: 973
    • 4c Kato M, Ogi D, Yao M, Misaki Y. Chem. Lett. 2013; 42: 1556
    • 4d Kato M, Senoo K, Yao M, Misaki Y. J. Mater. Chem. A 2014; 2: 6747
    • 4e Iwamoto S, Inatomi Y, Ogi D, Shibayama S, Murakami Y, Kato M, Takahashi K, Tanaka K, Hojo N, Misaki Y. Beilstein J. Org. Chem. 2015; 11: 1136
    • 4f Yamauchi T, Shibata Y, Aki T, Yoshimura A, Yao M, Misaki Y. Chem. Lett. 2018; 47: 1176
    • 4g Ogi D, Fujita Y, Kato M, Yamauchi T, Shirahata T, Yao M, Misaki Y. Eur. J. Org. Chem. 2019; 2725
    • 4h Yamauchi T, Kato M, Shirahata T, Yao M, Misaki Y. Chem. Lett. 2019; 48: 1507
    • 5a Akiba K, Ishikawa K, Inamoto N. Bull. Chem. Soc. Jpn. 1978; 51: 2674
    • 5b Bryce MR, Moore AJ. Synth. Met. 1988; 25: 203
    • 5c Bryce MR, Moore AJ, Hasan M, Ashwell GJ, Fraser AT, Clegg W, Hursthouse MB, Karaulov AI. Angew. Chem. Int. Ed. Engl. 1990; 29: 1450
    • 5d Barthelmes K, Sittig M, Winter A, Schubert US. Eur. J. Inorg. Chem. 2017; 3698
    • 5e Hachem H, Vacher A, Dorcet V, Lorcy D. Organometallics 2017; 36: 2208
    • 6a Bryce MR, Finn T, Moore AJ, Batsanov AS, Howard JA. K. Eur. J. Org. Chem. 2000; 51
    • 6b Jones AE, Christensen CA, Perepichka DF, Batsanov AS, Beeby A, Low PJ, Bryce MR, Parker AW. Chem. Eur. J. 2001; 7: 973
    • 7a Martín N, Sańchez L, Herranz MÁ, Illescas B, Guldi DM. Acc. Chem. Res. 2007; 40: 1015
    • 7b Wenger S, Bouit P.-A, Chen Q, Teuscher J, Censo DD, Humphry-Baker R, Moser J.-E, Delgado JL, Martín N, Zakeeruddin SM, Grätzel M. J. Am. Chem. Soc. 2010; 132: 5164
  • 8 See ref 4g.
    • 9a Hardouin-Lerouge M, Chesneau B, Allain M, Hudhomme P. J. Org. Chem. 2012; 77: 2441
    • 9b Isla H, Gallego M, Perez EM, Viruela R, Ortí E, Martín N. J. Am. Chem. Soc. 2010; 132: 1772
    • 9c Bivaud S, Goeb S, Croué V, Dron PI, Allain M, Sallé M. J. Am. Chem. Soc. 2013; 135: 10018
  • 10 Mitamura Y, Yorimitsu H, Oshima K, Osuka A. Chem. Sci. 2011; 2: 2017
    • 11a Bivaud S, Goeb S, Croué V, Allain M, Pop F, Sallé M. Beilstein J. Org. Chem. 2015; 11: 966
    • 11b Croué V, Goeb S, Szalóki G, Allain M, Sallé M. Angew. Chem. Int. Ed. 2016; 55: 1746
    • 11c Szalóki G, Croué V, Allain M, Goeb S, Sallé M. Chem. Commun. 2016; 52: 10012
    • 11d Szalóki G, Croué V, Carré V, Aubriet F, Alévêque O, Levillain E, Allain M, Aragó J, Ortí E, Goeb S, Sallé M. Angew. Chem. Int. Ed. 2017; 56: 16272
    • 11e Colomban C, Szalóki G, Allain M, Gómez L, Goeb S, Sallé M, Costas M, Ribas X. Chem. Eur. J. 2017; 23: 3016
    • 11f Szalóki G, Krykun S, Croué V, Allain M, Morille Y, Aubriet F, Carré V, Voitenko Z, Goeb S, Sallé M. Chem. Eur. J. 2018; 24: 11273
    • 12a Narayan TC, Miyakai T, Seki S, Dincă M. J. Am. Chem. Soc. 2012; 134: 12932
    • 12b Park SS, Hontz ER, Sun L, Hendon CH, Walsh A, Voorhis TV, Dincă M. J. Am. Chem. Soc. 2015; 137: 1774
    • 12c Chen B, Lv Z.-P, Leong CF, Zhao Y, D’Alessandro DM, Zuo J.-L. Cryst. Growth Des. 2015; 15: 1861
    • 12d Sun L, Park SS, Sheberla D, Dincă M. J. Am. Chem. Soc. 2016; 138: 14772
    • 12e Park SS, Hendon CH, Fielding AJ, Walsh A, O’Keeffe M, Dincă M. J. Am. Chem. Soc. 2017; 139: 3619
    • 12f Hisaki I, Affendy EN. Q, Tohnai N. CrystEngComm 2017; 19: 4892
    • 12g Su J, Yuan S, Wang H.-Y, Huang L, Ge J.-Y, Joseph E, Qin J, Cagin T, Zuo J.-L, Zhou H.-C. Nat. Commun. 2017; 8: 2008
    • 12h Park SS, Rieth AJ, Hendon CH, Dincă M. J. Am. Chem. Soc. 2018; 140: 2016
    • 12i Souto M, Romero J, Calbo J, Vitórica-Yrezábal IJ, Zafra JL, Casado J, Ortí E, Walsh A, Espallargas GM. J. Am. Chem. Soc. 2018; 140: 10562
    • 12j Souto M, Santiago-Portillo A, Palomino M, Vitórica-Yrezábal IJ, Vieira BJ. C, Waerenborgh JC, Valencia S, Navalón S, Rey F, García H, Espallargas GM. Chem. Sci. 2018; 9: 2413
    • 12k Leong CF, Wang C.-H, Ling CD, D’Alessandro DM. Polyhedron 2018; 154: 334
    • 12l Pattengale B, Neu J, Ostresh S, Hu G, Spies JA, Okabe R, Brudvig GW, Schmuttenmaer CA. J. Am. Chem. Soc. 2019; 141: 9793
    • 12m Castells-Gil J, Mañas-Valero S, Vitórica-Yrezábal IJ, Ananias D, Rocha J, Santiago R, Bromley ST, Baldoví JJ, Coronado E, Souto M, Espallargas GM. Chem. Eur. J. 2019; 25: 12636
    • 12n Su J, Hu T.-H, Murase R, Wang H.-Y, D’Alessandro DM, Kurmoo M, Zuo J.-L. Inorg. Chem. 2019; 58: 3698
    • 12o Cadiau A, Xie LS, Kolobov N, Shkurenko A, Qureshi M, Tchalala MR, Park SS, Bavykina A, Eddaoudi M, Dincă M, Henden CH, Gascon J. Chem. Mater. 2020; 32: 97
    • 12p Wang F, Wang J, Maehrlein SF, Ma Y, Liu F, Zhu X.-Y. J. Phys. Chem. Lett. 2020; 11: 762
    • 12q Su J, He W, Li X.-M, Sun L, Wang H.-Y, Lan Y.-Q, Ding M, Zuo J.-L. Matter 2020; 2: 711
  • 13 Cai S, Sun B, Li X, Yan Y, Navarro A, Garzón-Ruiz A, Mao H, Chatterjee R, Yano J, Zhu C, Reimer JA, Zheng S, Fan J, Zhang W, Liu Y. ACS Appl. Mater. Interfaces 2020; 12: 19054
    • 14a Wang H.-Y, Ge J.-J, Hua C, Jiao C.-Q, Wu Y, Leong CF, D’Alessandro DM, Liu T, Zuo J.-L. Angew. Chem. Int. Ed. 2017; 56: 5465
    • 14b Wang H.-Y, Su J, Ma J.-P, Yu F, Leong CF, D’Alessandro DM, Kurmoo M, Zuo J.-L. Inorg. Chem. 2019; 58: 8657
    • 14c Yu Q, Su J, Ma J.-P, Leong CF, D’Alessandro DM, Wang H.-Y, Kurmoo M, Zuo J.-L. Cryst. Growth Des. 2019; 19: 3012
  • 15 During the preparation of this manuscript, a paper about a double-helical MOF composed of a tetrabenzoic acid-TTFAQ ligand and a Zn metal node appeared: Gordillo MA, Benavides PA, Panda DK, Saha S. ACS Appl. Mater. Interfaces 2020; 12: 12955 . We also prepared a Zn-based MOF via the same procedure. The structure of the Zn-based MOF 3 prepared in this work is similar to the precedent work, however, there are slight differences (see the Supporting Information)
    • 16a Coucouvanis D, Reynolds RA. III, Dunham WR. J. Am. Chem. Soc. 1995; 117: 7570
    • 16b Aromí G, Batsanov AS, Christian P, Helliwell M, Parkin A, Parsons S, Smith AA, Timco GA, Winpenny RE. P. Chem. Eur. J. 2003; 9: 5142
  • 17 Chen B, Ockwig NW, Fronczek FR, Contreras DS, Yaghi OM. Inorg. Chem. 2005; 44: 181
  • 18 Alvarez S. Dalton Trans. 2013; 8617