Practical synthesis of 9-substituted triptycene derivatives

References

• Akio, S.; Fumio, O.; Masazumi, N. Synthesis of Trisubstituted Triptycenes and the Optical Resolution of 7-Carboxy-2, 5-diacetoxytriptycene. Bull. Chem. Soc. Jpn. 1962, 35, 853–857. DOI: 10.1246/bcsj.35.853.
   Web of Science ®Google Scholar
• Bartlett, P. D.; Ryan, M. J.; Cohen, S. G. Triptycene 1 (9,10-o-Benzenoanthracene). J. Am. Chem. Soc. 1942, 64, 2649–2653. DOI: 10.1021/ja01263a035.
   Google Scholar
• Wittig, G.; Benz, E. Triptycen Aus Dehydrobenzol Und Anthracen. Tetrahedron 1960, 10, 37–40. DOI: 10.1016/0040-4020(60)85004-1.
   Web of Science ®Google Scholar
• (a) Meng, H.; Zhao, C.; Nie, M.; Wang, C.; Wang, T. Triptycene Molecular Rotors Mounted on Metallofullerene Sc3C2@C80 and Their Spin-Rotation Couplings. Nanoscale 2018, 10, 18119–18123. DOI: 10.1039/C8NR06045B.
   PubMed Web of Science ®Google Scholar
  (b) Ube, H.; Yamada, R.; Ishida, J-i.; Sato, H.; Shiro, M.; Shionoya, M. A Circularly Arranged Sextuple Triptycene Gear Molecule. J. Am. Chem. Soc. 2017, 139, 16470–16473. DOI: 10.1021/jacs.7b09439.
   PubMed Web of Science ®Google Scholar
• Chen, C.-F.; Han, Y. Triptycene-Derived Macrocyclic Arenes: From Calixarenes to Helicarenes. Acc. Chem. Res. 2018, 51, 2093–2106. DOI: 10.1021/acs.accounts.8b00268.
   PubMed Web of Science ®Google Scholar
• (a) Corrado, T.; Huang, Z.; Aboki, J.; Guo, R. Microporous Polysulfones with Enhanced Separation Performance via Integration of the Triptycene Moiety. Ind. Eng. Chem. Res. 2020, 59, 5351–5361. DOI: 10.1021/acs.iecr.9b04861.
   Web of Science ®Google Scholar
  (b) Ikai, T.; Yoshida, T.; Shinohara, K-i.; Taniguchi, T.; Wada, Y.; Swager, T. M. Triptycene-Based Ladder Polymers with One-Handed Helical Geometry. J. Am. Chem. Soc. 2019, 141, 4696–4703. DOI: 10.1021/jacs.8b13865.
   PubMed Web of Science ®Google Scholar
• (a) Grossman, O.; Azerraf, C.; Gelman, D. Palladium Complexes Bearing Novel Strongly Bent Trans-Spanning Diphosphine Ligands: Synthesis, Characterization, and Catalytic Activity. Organometallics 2006, 25, 375–381. DOI: 10.1021/om050906j.
   Google Scholar
  (b) Azerraf, C.; Grossman, O.; Gelman, D. Rigid Trans-Spanning Triptycene-Based Ligands: How Flexible They Can Be? J. Organomet. Chem. 2007, 692, 761–767. DOI: 10.1016/j.jorganchem.2006.09.065.
   Web of Science ®Google Scholar
  (c) Azerraf, C.; Cohen, S.; Gelman, D. Roof-Shaped Halide-Bridged Bimetallic Complexes via Ring Expansion Reaction. Inorg. Chem. 2006, 45, 7010–7017. DOI: 10.1021/ic060700q.
   PubMed Web of Science ®Google Scholar
• Baumgärtner, K.; Rominger, F.; Mastalerz, M. An Oxidative Macrobicyclic Ring Opening of a Triptycene to a Highly Functionalized Fluorene Derivative. J. Org. Chem. 2015, 80, 8881–8886. DOI: 10.1021/acs.joc.5b01426.
   PubMed Web of Science ®Google Scholar
• (a) Zhao, L.; Li, Z.; Thomas Wirth, T. Triptycene Derivatives: Synthesis and Applications. Chem. Lett. 2010, 39, 658–667. DOI: 10.1246/cl.2010.658.
   Web of Science ®Google Scholar
  (b) Chong, J. H.; MacLachlan, M. J. Iptycenes in Supramolecular and Materials Chemistry. Chem. Soc. Rev. 2009, 38, 3301–3315. DOI: 10.1039/B900754g.
   PubMed Web of Science ®Google Scholar
  (c) Ma, Y.-X.; Meng, Z.; Chen, C.-F. Synthesis of Substituted Iptycenes. Synlett 2014, 26, 6–30. DOI: 10.1055/s-0034-1379361.
   Web of Science ®Google Scholar
• Zhang, C.; Chen, C.-F. Synthesis and Structure of 2,6,14- and 2,7,14-Trisubstituted Triptycene Derivatives. J. Org. Chem. 2006, 71, 6626–6629. DOI: 10.1021/jo061067t.
   PubMed Web of Science ®Google Scholar
• Yoon, I.; Suh, S.-E.; Barros, S. A.; Chenoweth, D. M. Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting. Org. Lett. 2016, 18, 1096–1099. DOI: 10.1021/acs.orglett.6b00169.
   PubMed Web of Science ®Google Scholar
• Iwata, T.; Hyodo, M.; Fukami, T.; Shiota, Y.; Yoshizawa, K.; Shindo, M. Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes. Chemistry 2020, 26, 8506–8510. DOI: 10.1002/chem.202002065.
   PubMed Web of Science ®Google Scholar
• (a) Ikai, T.; Nagata, N.; Awata, S.; Wada, Y.; Maeda, K.; Mizuno, M.; Swager, T. M. Optically Active Distorted Cyclic Triptycenes: chiral Stationary Phases for HPLC. RSC Adv. 2018, 8, 20483–20487. DOI: 10.1039/C8RA04434A.
   Web of Science ®Google Scholar
  (b) Aida, Y.; Shibata, Y.; Tanaka, K. Enantioselective Synthesis of Distorted π-Extended Chiral Triptycenes Consisting of Three Distinct Aromatic Rings by Rhodium-Catalyzed [2 + 2+2] Cycloaddition. Chemistry 2020, 26, 3004–3009. DOI: 10.1002/chem.201905519.
   PubMed Web of Science ®Google Scholar
  (c) Preda, G.; Nitti, A.; Pasini, D. Chiral Triptycenes in Supramolecular and Materials Chemistry. Chem. Open 2020, 9, 719–727. DOI: 10.1002/open.202000077.
   Google Scholar
• Kim, Y.; Zhu, Z.; Swager, T. M. Hyperconjugative and Inductive Perturbations in Poly(p-Phenylene Vinylenes). J. Am. Chem. Soc. 2004, 126, 452–453. DOI: 10.1021/ja038472b.
   PubMed Web of Science ®Google Scholar
• Zhu, X.-F.; Chen, C.-F. Iptycene Quinones: Synthesis and Structure. J. Org. Chem. 2005, 70, 917–924. DOI: 10.1021/jo0483015.
   PubMed Web of Science ®Google Scholar
• Matsumoto, K.; Nakano, R.; Hirokane, T.; Yoshida, M. Synthesis of Bridgehead-Functionalized Triptycene Quinones via Lewis Acid–Promoted Diels-Alder Reaction of 9-Acyloxyanthracenes. Tetrahedron Lett. 2019, 60, 975–978. DOI: 10.1016/j.tetlet.2019.03.001.
   Web of Science ®Google Scholar
• Rybáčková, M.; Bělohradský, M.; Holý, P.; Pohl, R.; Závada, J. Versatile Synthesis of Triptycene Di- and Tetracarboxylic Acids. Synthesis 2006, 12, 2039–2042. DOI: 10.1055/s-2006-942385.
   Google Scholar