1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization

References

• Long, T. M.; Swager, T. M. Minimization of Free Volume: Alignment of Triptycenes in Liquid Crystals and Stretched Polymers. Adv. Mater. 2001, 13, 601–604. DOI: 10.1002/1521-4095(200104)13:8<601::AID-ADMA601>3.0.CO;2-V.
   Web of Science ®Google Scholar
• Furuta, T.; Oka, K.; Tohnai, N. B. Construction of Triptycene Molecular Rotors with Intermeshing Arrangement and Low Rotational Barrier. Chem. Soc. Jpn. 2024, 97, uoae013. DOI: 10.1093/bulcsj/uoae013.
   Google Scholar
• Zhao, L.; Li, Z.; Wirth, T. Triptycene Derivatives: Synthesis and Applications. Chem. Lett. 2010, 39, 658–667. DOI: 10.1246/cl.2010.658.
   Web of Science ®Google Scholar
• Jiang, Y.; Chen, C.-F. Recent Developments in Synthesis and Applications of Triptycene and Pentiptycene Derivatives. Eur. J. Org. Chem. 2011, 2011, 6377–6403. DOI: 10.1002/ejoc.201100684.
   Web of Science ®Google Scholar
• Gu, M. J.; Wang, Y. F.; Han, Y.; Chen, C. F. Recent Advances on Triptycene Derivatives in Supramolecular and Materials Chemistry. Org. Biomol. Chem. 2021, 19, 10047–10067. DOI: 10.1039/d1ob01818c.
   PubMed Web of Science ®Google Scholar
• Krishnan Jagadamma, L.; McCarron, L. J.; Wiles, A. A.; Savikhin, V.; Sajjad, M. T.; Yazdani, M.; Rotello, V. M.; Toney, M. F.; Cooke, G.; Samuel, I. D. W. Triptycene as a Supramolecular Additive in PTB7:PCBM Blends and its Influence on Photovoltaic Properties. ACS Appl. Mater. Interfaces 2018, 10, 24665–24678. DOI: 10.1021/acsami.8b03114.
   PubMed Web of Science ®Google Scholar
• Li, H.; Chen, F.; Guan, X.; Li, J.; Li, C.; Tang, B.; Valtchev, V.; Yan, Y.; Qiu, S.; Fang, Q. Three-Dimensional Triptycene-Based Covalent Organic Frameworks with CEQ or ACS Topology. J. Am. Chem. Soc. 2021, 143, 2654–2659. DOI: 10.1021/jacs.0c12499.
   PubMed Web of Science ®Google Scholar
• Ishiwari, F.; Shoji, Y.; Martin, C. J.; Fukushima, T. Recent Advances in Structurally Elaborate Triptycenes, Triptycene-Containing Polymers and Assemblies: Structures, Functions and Applications. Polym. J. 2024. DOI: 10.1038/s41428-024-00920-x.
   Google Scholar
• Russell, G. A.; Suleman, N. K.; Iwamura, H.; Webster, O. W. Radical Anions of Triptycene Bis- and Tris(Quinones). J. Am. Chem. Soc. 1981, 103, 1560–1561. DOI: 10.1021/ja00396a046.
   Web of Science ®Google Scholar
• Shuku, Y.; Mizuno, A.; Ushiroguchi, R.; Hyun, C. S.; Ryu, Y. J.; An, B.-K.; Kwon, J. E.; Park, S. Y.; Tsuchiizu, M.; Awaga, K. An Exotic Band Structure of a Supramolecular Honeycomb Lattice Formed by a Pancake π–π Interaction Between Triradical Trianions of Triptycene Tribenzoquinone. Chem. Commun. 2018, 54, 3815–3818. DOI: 10.1039/C8CC00753E.
   PubMed Web of Science ®Google Scholar
• Shoji, Y.; Yamamoto, S.; Fukushima, T. Perchlorinated Triptycene Tribenzoquinone. Chem. Lett. 2021, 50, 1240–1243. DOI: 10.1246/cl.210219.
   Web of Science ®Google Scholar
• Takemasa, Y.; Nozaki, K. Synthesis of Triptycenemonohydroquinonedibenzoquinone by Comproportionation. J. Org. Chem. 2022, 87, 1502–1506. DOI: 10.1021/acs.joc.1c01683.
   PubMed Web of Science ®Google Scholar
• Kwon, J. E.; Hyun, C.-S.; Ryu, Y. J.; Lee, J.; Min, D. J.; Park, M. J.; An, B.-K.; Park, S. Y. Triptycene-Based Quinone Molecules Showing Multi-Electron Redox Reactions for Large Capacity and High Energy Organic Cathode Materials in Li-Ion Batteries. J. Mater. Chem. A 2018, 6, 3134–3140. DOI: 10.1039/C7TA09968A.
   Web of Science ®Google Scholar
• An, S. Y.; Schon, T. B.; Seferos, D. S. Stable, Dual Redox Unit Organic Electrodes. ACS Omega. 2020, 5, 1134–1141. DOI: 10.1021/acsomega.9b03355.
   PubMed Web of Science ®Google Scholar
• Park, H.; Shuku, Y.; Lee, J.; Lee, K.; Min, D. J.; An, B.-K.; Awaga, K.; Park, S. Y.; Kwon, J. E. Isomeric Triptycene Triquinones as Universal Cathode Materials for High Energy Alkali Metal Batteries. Batter. Supercaps 2023, 6, e202200497. DOI: 10.1002/batt.202200497.
   Google Scholar
• Zhu, X. Z.; 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
• 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
• Norvez, S.; Tournilhac, F. G.; Bassoul, P.; Herson, P. Mesomorphism and Polar Distortion in 1,4,5,8-Tetrasubstituted Anthraquinones and Anthracenes. Chem. Mater. 2001, 13, 2552–2561. DOI: 10.1021/cm0009064.
   Web of Science ®Google Scholar
• Ryu, Y.; Hyun, C.-S.; An, B.-K. Practical Synthesis of Triptycene Trisquinone. Synth. Commun. 2022, 52, 1184–1189. DOI: 10.1080/00397911.2022.2077115.
   Web of Science ®Google Scholar
• Iwamura, H.; Makino, K. 5,8-Dihydroxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione. An Intramolecular Triptycene Quinhydrone. J. Chem. Soc. Chem. Commun. 1978, 720–721. DOI: 10.1039/c39780000720.
   Google Scholar
• Mistry, J.-R.; Montanaro, S.; Wright, I. A. Homoconjugation Effects in Triptycene Based Organic Optoelectronic Materials. Mater. Adv 2023, 4, 787–803. DOI: 10.1039/D2MA00523A.
   Google Scholar
• Baumgärtner, K.; Hoffmann, M.; Rominger, F.; Elbert, S. M.; Dreuw, A.; Mastalerz, M. Homoconjugation and Intramolecular Charge Transfer in Extended Aromatic Triptycenes with Different π-Planes. J. Org. Chem. 2020, 85, 15256–15272. DOI: 10.1021/acs.joc.0c02100.
   PubMed Web of Science ®Google Scholar
• Lei, P.; Zhang, S.; Zhang, N.; Yin, X.; Wang, N.; Chen, P. Triptycene-Based Luminescent Materials in Homoconjugated Charge-Transfer Systems: Synthesis, Electronic Structures, AIE Activity, and Highly Tunable Emissions. ACS Omega. 2020, 5, 28606–28614. DOI: 10.1021/acsomega.0c03565.
   PubMed Web of Science ®Google Scholar
• Qian, R.; Tong, H.; Huang, C.; Li, J.; Tang, Y.; Wang, R.; Lou, K.; Wang, W. A Donor-Acceptor Triptycene-Coumarin Hybrid Dye Featuring a Charge Separated Excited State and AIE Properties. Org. Biomol. Chem. 2016, 14, 5007–5011. DOI: 10.1039/c6ob00822d.
   PubMed Web of Science ®Google Scholar
• Montanaro, S.; Pander, P.; Mistry, J. R.; Elsegood, M. R. J.; Teat, S. J.; Bond, A. D.; Wright, I. A.; Congrave, D. G.; Etherington, M. K. Simultaneous Enhancement of Thermally Activated Delayed Fluorescence and Photoluminescence Quantum Yield via Homoconjugation. J. Mater. Chem. C 2022, 10, 6306–6313. DOI: 10.1039/D2TC00460G.
   Web of Science ®Google Scholar
• Meng, D.; Fu, H.; Fan, B.; Zhang, J.; Li, Y.; Sun, Y.; Wang, Z. Rigid Nonfullerene Acceptors Based on Triptycene–Perylene Dye for Organic Solar Cells. Chem. Asian J. 2017, 12, 1286–1290. DOI: 10.1002/asia.201700440.
   PubMed Web of Science ®Google Scholar
• Lv, L.; Sun, W.; Jia, Z.; Zhang, G.; Wang, F.; Tan, Z.; Zhang, L. Perylene Monoimide and Naphthalene-Annulated [3,3,3]Propellanes: Synthesis and Device Applications. Mater. Chem. Front. 2020, 4, 3539–3545. DOI: 10.1039/C9QM00668K.
   Web of Science ®Google Scholar
• Bui, A. T.; Hartley, N. A.; Thom, A. J.; Forse, A. C. Trade-Off Between Redox Potential and the Strength of Electrochemical CO2 Capture in Quinones. J. Phys. Chem. C 2022, 126, 14163–14172. DOI: 10.1021/acs.jpcc.2c03752.
   PubMed Web of Science ®Google Scholar