Synthesis and structural characterization of two rotationally flexible bis(benzoxaphosphole)s

References

• Bates, J. I.; Dugal-Tessier, J.; Gates, D. P. Phospha-Organic Chemistry: From Molecules to Polymers. Dalt. Trans. 2010, 39, 3151–3159. DOI: 10.1039/B918938F.
   PubMed Web of Science ®Google Scholar
• Hissler, M.; Lescop, C.; Réau, R. Functional Phosphorus-Based π-Conjugated Systems: Structural Diversity without Multistep Synthesis. Pure Appl. Chem. 2007, 79, 201–212. DOI: 10.1351/pac200779020201.
   Web of Science ®Google Scholar
• Pfeifer, G.; Chahdoura, F.; Papke, M.; Weber, M.; Szűcs, R.; Geffroy, B.; Tondelier, D.; Nyulászi, L.; Hissler, M.; Müller, C. Synthesis, Electronic Properties and OLED Devices of Chromophores Based on λ 5 ‐Phosphinines. Chem. Eur. J. 2020, 26, 10534–10543. DOI: 10.1002/chem.202000932.
   PubMed Web of Science ®Google Scholar
• Hirai, M.; Tanaka, N.; Sakai, M.; Yamaguchi, S. Structurally Constrained Boron-, Nitrogen-, Silicon-, and Phosphorus-Centered Polycyclic π-Conjugated Systems. Chem. Rev. 2019, 119, 8291–8331.
   PubMed Web of Science ®Google Scholar
• Baumgartner, T.; Réau, R. Organophosphorus π-Conjugated Materials. Chem. Rev. 2006, 106, 4681–4727.
   PubMed Web of Science ®Google Scholar
• Chen, H.; Delaunay, W.; Yu, L.; Joly, D.; Wang, Z.; Li, J.; Wang, Z.; Lescop, C.; Tondelier, D.; Geffroy, B.; et al. 2,2′-Biphospholes: Building Blocks for Tuning the HOMO-LUMO Gap of π-Systems Using Covalent Bonding and Metal Coordination. Angew. Chem. Int. Ed. Engl. 2012, 51, 214–217. DOI: 10.1002/anie.201105924.
   PubMed Web of Science ®Google Scholar
• Simpson, M. C.; Protasiewicz, J. D. Phosphorus as a Carbon Copy and as a Photocopy: New Conjugated Materials Featuring Multiply Bonded Phosphorus. Pure Appl. Chem. 2013, 85, 801–815. DOI: 10.1351/PAC-CON-12-09-13.
   Web of Science ®Google Scholar
• Karabunarliev, S.; Baumgarten, M.; Tyutyulkov, N.; Muellen, K. Structure and Optical Absorption of Oligo(p- and m-Phenylenevinylenes) and Their Radical Anions: A Comparative Theoretical Study. J. Phys. Chem. 1994, 98, 11892–11901. DOI: 10.1021/j100097a015.
   Web of Science ®Google Scholar
• Mathey, F. Phospha-Organic Chemistry: Panorama and Perspectives. Angew. Chem. Int. Ed. Engl. 2003, 42, 1578–1604.
   PubMed Web of Science ®Google Scholar
• Priegert, A. M.; Rawe, B. W.; Serin, S. C.; Gates, D. P. Polymers and the P-Block Elements. Chem. Soc. Rev. 2016, 45, 922–953.
   PubMed Web of Science ®Google Scholar
• Mathey, F. Expanding the Analogy between Phosphorus-Carbon and Carbon-Carbon Double Bonds. Acc. Chem. Res. 1992, 25, 90–96. DOI: 10.1021/ar00014a006.
   Web of Science ®Google Scholar
• Wu, S.; Rheingold, A. L.; Golen, J. A.; Grimm, A. B.; Protasiewicz, J. D. Synthesis of a Luminescent Azaphosphole. Eur. J. Inorg. Chem. 2016, 2016, 768–773. DOI: 10.1002/ejic.201501279.
   Google Scholar
• Worch, J. C.; Chirdon, D. N.; Maurer, A. B.; Qiu, Y.; Geib, S. J.; Bernhard, S.; Noonan, K. J. T. Synthetic Tuning of Electronic and Photophysical Properties of 2-Aryl-1,3-Benzothiaphospholes. J. Org. Chem. 2013, 78, 7462–7469.
   PubMed Web of Science ®Google Scholar
• Washington, M. P.; Gudimetla, V. B.; Laughlin, F. L.; Deligonul, N.; He, S.; Payton, J. L.; Simpson, M. C.; Protasiewicz, J. D. Phosphorus Can Also Be a “Photocopy.” J. Am. Chem. Soc. 2010, 132, 4566–4567. DOI: 10.1021/ja1009426.
   PubMed Web of Science ®Google Scholar
• Ito, S.; Koshino, K.; Mikami, K. CF3-Inspired Synthesis of Air-Tolerant 9-Phosphaanthracenes That Feature Fluorescence and Crystalline Polymorphs. Chem. Asian J. 2018, 13, 830–837. DOI: 10.1002/asia.201701669.
   PubMed Web of Science ®Google Scholar
• Sklorz, J. A. W.; Hoof, S.; Rades, N.; De Rycke, N.; Könczöl, L.; Szieberth, D.; Weber, M.; Wiecko, J.; Nyulászi, L.; Hissler, M.; Müller, C. Pyridyl-Functionalised 3H-1,2,3,4-Triazaphospholes: Synthesis, Coordination Chemistry and Photophysical Properties of Low-Coordinate Phosphorus Compounds. Chem. Eur. J. 2015, 21, 11096–11109. DOI: 10.1002/chem.201500988.
   PubMed Web of Science ®Google Scholar
• Nagahora, N.; Goto, S.; Inatomi, T.; Tokumaru, H.; Matsubara, K.; Shioji, K.; Okuma, K. Buchwald–Hartwig Amination of Phosphinines and the Effect of Amine Substituents on Optoelectronic Properties of the Resulting Coupling Products. J. Org. Chem. 2018, 83, 6373–6381.
   PubMed Web of Science ®Google Scholar
• Qiu, Y.; Worch, J. C.; Chirdon, D. N.; Kaur, A.; Maurer, A. B.; Amsterdam, S.; Collins, C. R.; Pintauer, T.; Yaron, D.; Bernhard, S.; Noonan, K. J. T. Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes. Chem. Eur. J. 2014, 20, 7746–7751. DOI: 10.1002/chem.201402561.
   PubMed Web of Science ®Google Scholar
• Wu, S.; Rheingold, A. L.; Protasiewicz, J. D. Luminescent Materials Containing Multiple Benzoxaphosphole Units. Chem. Commun. (Camb.) 2014, 50, 11036–11038.
   PubMed Web of Science ®Google Scholar
• Ndimba, A.; Roisnel, T.; Argouarch, G.; Lalli, C. Harvesting New Chiral Phosphotriesters by Phosphorylation of BINOL and Parent Bis-Phenols. Synthesis (Stuttg) 2019, 51, 865–873.
   Web of Science ®Google Scholar
• Grimm, A. B.; Wang, K.; Rheingold, A. L.; Moore, C. E.; Szieberth, D.; Nyulászi, L.; Protasiewicz, J. D. 2-Aryl-1,3-Benzoxaphospholes as Unwilling Participants for Catalytic Suzuki–Miyaura CC Coupling Reactions. Organometallics 2021, 40, 3436–3444. DOI: 10.1021/acs.organomet.1c00462.
   Web of Science ®Google Scholar
• Hausen, H.-D.; Weckler, G. 2-p-Chlorphenyl-1,3-benzoxaphosphol Molekül- und Kristallstruktur eines σ2—P=C—O-Derivates. Z. anorg. allg. Chem. 1985, 520, 107–112. DOI: 10.1002/zaac.19855200114.
   Google Scholar
• Li, H.; Wei, K.; Wu, Y.-J. A Convenient Synthesis of 2-Arylnaphtho[1,2-d]Oxazole Derivatives Promoted by Triethylamine. Chin. J. Chem. 2007, 25, 1704–1709. DOI: 10.1002/cjoc.200790315.
   Web of Science ®Google Scholar
• Baumgardt, I.; Butenschön, H. 1,1′-Diaryl-Substituted Ferrocenes: Up to Three Hinges in Oligophenyleneethynylene-Type Molecular Wires. Eur. J. Org. Chem. 2010, 2010, 1076–1087. DOI: 10.1002/ejoc.200901252.
   Web of Science ®Google Scholar
• Ogawa, S.; Kobayashi, H.; Muraoka, H. Synthesis, Structure, and Redox Properties of 1,1′-Bis(Aryloligothienyl)Ferrocenes. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 1238–1245. DOI: 10.1080/10426507.2010.524178.
   Web of Science ®Google Scholar
• Luo, Q.; Zhang, R.; Zhang, J.; Xia, J. Synthesis of Conjugated Main-Chain Ferrocene-Containing Polymers through Melt-State Polymerization. Organometallics 2019, 38, 2972–2978. DOI: 10.1021/acs.organomet.9b00312.
   Web of Science ®Google Scholar
• Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García, J.; Cohen, A. J.; Yang, W. Revealing Noncovalent Interactions. J. Am. Chem. Soc. 2010, 132, 6498–6506.
   PubMed Web of Science ®Google Scholar
• Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer. J. Comput. Chem. 2012, 33, 580–592.
   PubMed Web of Science ®Google Scholar
• Humphrey, W.; Dalke, A.; Schulten, K. VMD: Visual Molecular Dynamics. J. Mol. Graph. 1996, 14, 33–38.
   PubMed Web of Science ®Google Scholar
• Blanchard, M. D.; Hughes, R. P.; Concolino, T. E.; Rheingold, A. L. π-Stacking between Pentafluorophenyl and Phenyl Groups as a Controlling Feature of Intra- and Intermolecular Crystal Structure Motifs in Substituted Ferrocenes. Observation of Unexpected Face-to-Face Stacking between Pentafluorophenyl Rings. Chem. Mater. 2000, 12, 1604–1610. DOI: 10.1021/cm000093j.
   Web of Science ®Google Scholar
• Mata, J. A.; Peris, E.; Llusar, R.; Uriel, S.; Cifuentes, M. P.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B. Syntheses, Structures and Nonlinear Optical Properties of Ferrocenyl Complexes with Arylethenyl Substituents. Eur. J. Inorg. Chem. 2001, 2001, 2113–2122. DOI: 10.1002/1099-0682(200108)2001:8<2113::AID-EJIC2113>3.0.CO;2-I.
   Google Scholar
• Enders, M.; Kohl, G.; Pritzkow, H. Synthesis and Coordination Behaviour of the New (8-Quinolyl)Cyclopentadienyl Ligand. J. Organomet. Chem. 2001, 622, 66–73. DOI: 10.1016/S0022-328X(00)00866-4.
   Web of Science ®Google Scholar
• Anderson, J. C.; White, C.; Stenson, K. P. Synthesis of Ferrocene Bridged Bis (2-Indenyl) Ligands. Synlett 2002, 2002, 1511–1513. DOI: 10.1055/s-2002-33524.
   Google Scholar
• Fery-Forgues, S.; Delavaux-Nicot, B. Ferrocene and Ferrocenyl Derivatives in Luminescent Systems. J. Photochem. Photobiol. A Chem. 2000, 132, 137–159. DOI: 10.1016/S1010-6030(00)00213-6.
   Web of Science ®Google Scholar
• Donoli, A.; Bisello, A.; Cardena, R.; Crisma, M.; Orian, L.; Santi, S. Charge Transfer Properties of Benzo [b] Thiophene Ferrocenyl Complexes. Organometallics 2015, 34, 4451–4463. DOI: 10.1021/acs.organomet.5b00191.
   Web of Science ®Google Scholar
• Lima, C. F. R. A. C.; Fernandes, A. M.; Melo, A.; Gonçalves, L. M.; Silva, A. M. S.; Santos, L. M. N. B. F. Diarylferrocene Tweezers for Cation Binding. Phys. Chem. Chem. Phys. 2015, 17, 23917–23923.
   PubMed Web of Science ®Google Scholar
• Sivaev, I. Ferrocene and Transition Metal Bis(Dicarbollides) as Platform for Design of Rotatory Molecular Switches. Molecules 2017, 22, 2201. DOI: 10.3390/molecules22122201.
   Web of Science ®Google Scholar
• Takai, A.; Yasuda, T.; Ishizuka, T.; Kojima, T.; Takeuchi, M. A Directly Linked Ferrocene-Naphthalenediimide Conjugate: Precise Control of Stacking Structures of π-Systems by Redox Stimuli. Angew. Chem. Int. Ed. Engl. 2013, 52, 9167–9171. DOI: 10.1002/anie.201302587.
   PubMed Web of Science ®Google Scholar
• Maniappan, S.; Jadhav, A. B.; Kumar, J. Template Assisted Generation of Chiral Luminescence in Organic Fluorophores. Front. Chem. 2021, 8, 1–7. DOI: 10.3389/fchem.2020.557650.
   Web of Science ®Google Scholar
• Kumar, J.; Nakashima, T.; Kawai, T. Circularly Polarized Luminescence in Chiral Molecules and Supramolecular Assemblies. J. Phys. Chem. Lett. 2015, 6, 3445–3452.
   PubMed Web of Science ®Google Scholar
• Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. Imidazole-Annelated Ferrocene Derivatives as Highly Selective and Sensitive Multichannel Chemical Probes for Pb(II) Cations. J. Org. Chem. 2009, 74, 4787–4796.
   PubMed Web of Science ®Google Scholar
• Couillens, X.; Gressier, M.; Coulais, Y.; Dartiguenave, M. Synthesis and Physicochemical Characterization of Oxo and Phenylimido Re(V), Re(III) and Ni(II) Complexes with the 2-[Bis(Ethoxyethyl)Phosphino]Phenolato Ligand and Derivatives. Inorganica Chim. Acta 2004, 357, 195–201. DOI: 10.1016/S0020-1693(03)00388-8.
   Web of Science ®Google Scholar
• Gao, B.; Yang, B.; Li, T.; Zhang, B. Synthesis and Characterization of Ester Ferrocenophanes. Synth. Commun. 2009, 39, 2973–2981. DOI: 10.1080/00397910802716150.
   Web of Science ®Google Scholar