Synthesis and optical properties, including fluorosolvatochromic and ICT-based proton-sensing behaviors of a series of 2,4,6-tris(5-aryl-2-thienyl)pyridines

References

• Meier, H.; Huang, Z.-S.; Cao, D. Double D-π-A Branched Dyes - A New Class of Metal-Free Organic Dyes for Efficient Dye-Sensitized Solar Cells. J. Mater. Chem. C. 2017, 5, 9828–9837. DOI: 10.1039/C7TC03406G.
   Web of Science ®Google Scholar
• Kim, T.-D.; Lee, K.-S. D-π-A Conjugated Molecules for Optoelectronic Applications. Macromol. Rapid Commun. 2015, 36, 943–958. DOI: 10.1002/marc.201400749.
   PubMed Web of Science ®Google Scholar
• Ooyama, Y.; Ohshita, J.; Harima, Y. Control of Molecular Arrangement and/or Orientation of D-π-A Fluorescent Dyes for Dye-Sensitized Solar Cells. Chem. Lett. 2012, 41, 1384–1396. DOI: 10.1246/cl.2012.1384.
   Web of Science ®Google Scholar
• Guo, Z.; Zhu, W.; Tian, H. Dicyanomethylene-4H-Pyran Chromophores for OLED Emitters, Logic Gates and Optical Chemosensors. Chem. Commun. 2012, 48, 6073–6084. DOI: 10.1039/c2cc31581e.
   PubMed Web of Science ®Google Scholar
• Enoki, T.; Ohshita, J.; Ooyama, Y. Synthesis and Photophysical and Electrochemical Properties of Structural Isomers of Pyrazine-Based D-π-A-π-D Fluorescent Dyes. BCSJ. 2018, 91, 1704–1709. DOI: 10.1246/bcsj.20180210.
   Google Scholar
• Fecková, M.; Le Poul, P.; Guen, F. R-l.; Roisnel, T.; Pytela, O.; Klikar, M.; Bureš, F.; Achelle, S. 2,4-Distyryl- and 2,4,6-Tristyrylpyrimidines: Synthesis and Photophysical Properties. J. Org. Chem. 2018, 83, 11712–11726. DOI: 10.1021/acs.joc.8b01653.
   PubMed Web of Science ®Google Scholar
• Verbitskiy, E. V.; Dinastiya, E. M.; Baranova, A. A.; Khokhlov, K. O.; Chuvashov, R. D.; Yakovleva, Y. A.; Makarova, N. I.; Vetrova, E. V.; Metelitsa, A. V.; Slepukhin, P. A.; et al. New V-Shaped 2,4-di(Hetero)Arylpyrimidine Push-Pull Systems: Synthesis, Solvatochromism and Sensitivity towards Nitroaromatic Compounds. Dyes Pigm. 2018, 159, 35–44. DOI: 10.1016/j.dyepig.2018.05.075.
   Web of Science ®Google Scholar
• Valeur, B.; Leray, I. Design Principles of Fluorescent Molecular Sensors for Cation Recognition. Coordin. Chem. Rev. 2000, 205, 3–40. DOI: 10.1016/S0010-8545(00)00246-0.
   Web of Science ®Google Scholar
• de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515–1566. DOI: 10.1021/cr960386p.
   PubMed Web of Science ®Google Scholar
• Muraoka, H.; Obara, T.; Ogawa, S. Systematic Synthesis, Comparative Studies of the Optical Properties, and the ICT-Based Sensor Properties of a Series of 2,4,6-Tri(5-Aryl-2-Thienyl)Pyrimidines with the D-π-A System. Tetrahedron Lett. 2016, 57, 3011–3015. DOI: 10.1016/j.tetlet.2016.05.099.
   Web of Science ®Google Scholar
• Muraoka, H.; Mori, M.; Ogawa, S. A Comparative Study of the Electronic Property of a Series of 2,4,6-Tri(5-Aryl-2-Thienyl)-1,3,5-Triazines Controlled by the Electronic Nature of Aryl Groups. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1382–1391. DOI: 10.1080/10426507.2015.1043047.
   Web of Science ®Google Scholar
• Hosokai, T.; Muraoka, H.; Mori, M.; Kurihara, R.; Ogawa, S.; Yoshimoto, N. Characterization of Aryl-Functionalized 2,4,6-Tris(2-Thienyl)-1,3,5-Triazine Thin Films and Their Application to Organic Field-Effect Transistors. Jpn. J. Appl. Phys. 2014, 53, 01AB15. DOI: 10.7567/JJAP.53.01AB15.
   Web of Science ®Google Scholar
• Nenner, I.; Schulz, G. J. Temporary Negative Ions and Electron Affinities of Benzene and N-Heterocyclic Molecules: pyridine, Pyridazine, Pyrimidine, Pyrazine, and s-Triazine. J. Chem. Phys. 1975, 62, 1747–1758. DOI: 10.1063/1.430700.
   Web of Science ®Google Scholar
• Namboodiri, C. K. R.; Bisht, P. B.; Mukkamala, R.; Chandra, B.; Aidhen, I. S. Solvatochromism, Multiphoton Fluorescence, and Resonance Energy Transfer in a New Octupolar Dye-Pair. Chem. Phys. 2013, 415, 190–195. DOI: 10.1016/j.chemphys.2013.01.012.
   Web of Science ®Google Scholar
• Bera, M. K.; Hommes, P.; Reissig, H.-U. In Search of Oligo(2-Thienyl)-Substituted Pyridine Derivatives: A Modular Approach to Di-, Tri- and Tetra(2-Thienyl)Pyridines. Chem. Eur. J. 2011, 17, 11838–11843. DOI: 10.1002/chem.201101739.
   PubMed Web of Science ®Google Scholar
• Thapa, P.; Karki, R.; Yun, M.; Kadayat, T. M.; Lee, E.; Kwon, H. B.; Na, Y.; Cho, W.-J.; Kim, N. D.; Jeong, B.-S.; et al. Design, Synthesis, and Antitumor Evaluation of 2,4,6-Triaryl Pyridines Containing Chlorophenyl and Phenolic Moiety. Eur. J. Med. Chem. 2012, 52, 123–136. DOI: 10.1016/j.ejmech.2012.03.010.
   PubMed Web of Science ®Google Scholar
• Suzuki, A. Cross-Coupling Reactions of Organoboranes: An Easy Way to Construct C-C Bonds (Nobel Lecture). Angew. Chem. Int. Ed. 2011, 50, 6723–6737. DOI: 10.1002/anie.201101379.
   Web of Science ®Google Scholar
• Miyaura, N. Metal-Catalyzed Cross-Coupling Reactions, Second, Completely Revised and Enlarged Edition, de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, pp 41–123.
   Google Scholar