π-сопряженные 4,6-дизамещенные пиримидины на основе 2-амино-4,6-диметилпиримидина: синтез и исследование их оптических и электрохимических характеристик
DOI:
https://doi.org/10.17072/2223-1838-2019-2-171-183Аннотация
Синтезирован ряд 4,6-дизамещенных 2-аминопиримидинов, содержащих протяженную цепь сопряжения, исследованы их оптические и электрохимические свойства. Показано, что соединениям свойственен положительный сольватохромизм, ацидохромизм, а также низкие значения потенциалов окисления, 2-амино-4,6-ди(2-гетарилвинил)пиримидины, включающие 1-метил-1Н-пиррольный и 10-гексил-10Н-фенотиазиновые фрагменты обладают низкой шириной запрещенной зоны: Egopt = 1,75 эВ (ТГФ) и 1.93 эВ (CHCl3); Egelc =1,11 и 0. 88 эВ, соответственноБиблиографические ссылки
Библиографический список
Hadad C., Achelle S., García-Martinez J.C., Rodríguez-Lopez J. 4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: Synthesis and Optical Properties // Journal of Organic Chemistry. 2011. Vol. 76, no. pp.3837-3845.
Vulpeş D., Chiriac A. Synthesis and Spectroscopic Properties of New Pyrimidinic Azo-Dyes // Annals of West University of Timisoara. Series of Chemistry. 2009. Vol.18, no. 1. pp. 53-60.
Mamtimin X., Aikebaierjiang A., Alifujiang M., Tuerxun T., Kurban Z., Sun W. F., Nurulla I. Synthesis, characterization and acidochromism of Poly (2-N,N–dimethylamino-4,6-Bis (2-thienyl)-pyrimidine) // Journal of Polymer Research. 2011. Vol. 1, no. 1. pp. 105-109.
Theodorou V., Gogou M., Giannousi A., Skobridis K. Insights into the N,N-diacylation reaction of 2-aminopyrimidines and deactivated anilines: an alternative N-monoacylation reaction // Arkivoc. 2014. no iv. pp.11-23.
Е.А. Комиссарова, И.В. Лунегов, О.А. Майорова, Е.В. Шкляева, Абашев Г.Г. Синтез и исследование новых поли(ариленвиниленов), включающих 2-замещенные пиримидиновые фрагменты // Изв. АН, Серия хим., 2016, 65(9), 2291-2298
Комиссарова Е.А., Лунегов И.В., Майорова О.А., Шкляева Е.В., Абашев Г.Г. Синтез 2-алкокси-4,6-ди(2-фенилвинил) пиримидинов, содержащих терминальные ТТФ-фрагменты // Бутлеровские сообщения. 2015. Vol. 42, no 4. pp. 55-60.
Komissarova E.A., Lunegov I.V., Shklyaeva E.V., Abashev G.G., Synthesis of novel pyrimidine derivatives of D-[π]-D type containing heterocycles and TTF moieties // 3rd International Fall School “Organic Electronics” (IFSOE-2016), 17-23 Sept. 2016, Moscow. p. 82.
E.A. Komissarova, E.A. Sosnin, E.V. Shklyaeva, I.V. Osorgina, G.G. Abashev. Synthesis of novel Y-shaped asymmetrical conjugated 2,4,6-trisubstituted pyrimidines and investigation of their optical and electrochemical properties // Arkivoc, 2017. no. iii. pp. 105-120.
Olugbade T.A., Usifoh C.O., Oluwadiya J.O., Reisch J. The reaction of amines with isoflavones. 2. Formation of phenolic sulfoamidopyrimidines // Journal of Heterocyclic. Chemistry. 1990. Vol.2, no 6. pp.1727-1728.
Liu В., Hu X.L., Liu J., Zhao Y.D., Huang Z.L. Synthesis and photophysical properties of novel pyrimidine-based two-photon absorption chromophores. // Tetrahedron. 2007. Vol.48. pp. 5958–596.
Cho N.S., Park J.H., Lee S.K., Lee J., Shim H.K. Saturated and Efficient Red Light-Emitting Fluorene-Based Alternating Polymers Containing Phenothiazine Derivatives // Macromolecules. 2006. Vol. 39, no 1. pp.177-183.
Zou Y., Wu W., Sang G., Yang Y., Liu Y., Li Y. Polythiophene Derivative with Phenothiazine−Vinylene Conjugated Side Chain: Synthesis and Its Application in Field-Effect Transistors // Macromolecules. 2007. Vol. 40. No 20. pp. 7231-7237.
Райхардт К., Растворители и эффекты среды в органической химии, М.:Мир, 1991, C.763.
Šulcová N., Nêmec I., Waisser K., Kies H.L. Study of the Electrochemical Oxidation of Phenothiazine Derivatives in Acetonitrile Medium: The Effect of the Structure on the Voltammetric Behavior // Microchemical Journal. 1980. Vol. 25, no. 4. pp. 551-566.
Pluczyk S., Zassowski P., Quinton C., Audebert P., Alain‐Rizzo V., Lapkowski M. The influence of the linker on electrochemical and spectroelectrochemical properties of donor-acceptor-donor triphenylamine-s-tetrazine derivatives // Electrochimica Acta. 2016. Vol. 216, no. pp. 160-170.
He Y., Qi Z., Yu J., Wang X., Wie B., Sun Y. Synthesis, characterization, and optical properties of a novel alternating 3-dodecyloxythiophene-co-pyridine copolymer // Polymer Bulletin. 2009. Vol. 62. pp. 139-149.
Li K.-C., Hsu Y.-C., Lin J.-T., Yang C.-C., Wei K.-H., Lin H.-C. Novel Narrow-Band-Gap Conjugated Copolymers Containing Phenothiazine-Arylcyanovinyl Units for Organic Photovoltaic Cell Applications // Journal of Polymer Science: Part A: Polymer Chemistry. 2008. Vol.46, no. 13. pp. 4285-4301
__________________
References
Hadad C., Achelle S., García-Martinez J.C., Rodríguez-Lopez J. (2011), “4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: Synthesis and Optical Properties”, Journal of Organic Chemistry. Vol. 76, no. pp.3837-3845.
Vulpeş D., Chiriac A. (2009), “Synthesis and Spectroscopic Properties of New Pyrimidinic Azo-Dyes”, Annals of West University of Timisoara. Series of Chemistry. Vol.18, no. 1. pp. 53-60.
Mamtimin X., Aikebaierjiang A., Alifujiang M., Tuerxun T., Kurban Z., Sun W. F., Nurulla I. (2011), Synthesis, characterization and acidochromism of Poly (2-N,N–dimethylamino-4,6-Bis (2-thienyl)-pyrimidine), Journal of Polymer Research. Vol. 1, no. 1. pp. 105-109.
Theodorou V., Gogou M., Giannousi A., Skobridis K. (2014), “Insights into the N,N-diacylation reaction of 2-aminopyrimidines and deactivated anilines: an alternative N-monoacylation reaction”, Arkivoc.no iv. pp. 11-23.
Komissarova Е.А., Lunegov I.V., Mayorova O.A., Shklyaeva E.V.,Abashev G.G. (2016), “Synthesis and investigation of poly(arylenevinylene)s, containing 2-substituted pyrimidine fragments”, Russian Chemical Bulletin. Vol. 65, no. 9. 2291-2298.
Komissarova Е.А., Lunegov I.V., Mayorova O.A., Shklyaeva E.V.,Abashev G.G. (2015), “Synthesis of 2-alkoxyи-4,6-di(2-phenylvinyl)pyrimidines, containing terminal TTF-fragments”, Butlerov Communications. Vol. 42, no 4. pp. 55-60 (In Rus.).
Komissarova E.A., Lunegov I.V., Shklyaeva E.V., Abashev G.G. (2016), “Synthesis of novel pyrimidine derivatives of D-[π]-D type containing heterocycles and TTF moieties”, Proceedings of the 3rd International Fall School “Organic Electronics” (IFSOE-2016), 17-23 Sept. 2016, Moscow. p. 82.
Komissarova E.A., Sosnin E.A., Shklyaeva E.V., Osorgina I.V., Abashev G.G. (2017), “Synthesis of novel Y-shaped asymmetrical conjugated 2,4,6-trisubstituted pyrimidines and investigation of their optical and electrochemical properties”, Arkivoc. no. iii. pp. 105-120.
Olugbade T.A., Usifoh C.O., Oluwadiya J.O., Reisch J. (1990), “The reaction of amines with isoflavones. 2. Formation of phenolic sulfoamidopyrimidines”, Journal of Heterocyclic. Chemistry. Vol.2, no 6. pp. 1727-1728.
Liu В., Hu X.L., Liu J., Zhao Y.D., Huang Z.L. (2007), “Synthesis and photophysical properties of novel pyrimidine-based two-photon absorption chromophores”, Tetrahedron. Vol.48. pp. 5958–5962.
Cho N.S., Park J.H., Lee S.K., Lee J., Shim H.K. (2006), “Saturated and Efficient Red Light-Emitting Fluorene-Based Alternating Polymers Containing Phenothiazine Derivatives”, Macromolecules. Vol. 39, no 1. pp.177-183.
Zou Y., Wu W., Sang G., Yang Y., Liu Y., Li Y. (2007), “Polythiophene Derivative with Phenothiazine−Vinylene Conjugated Side Chain: Synthesis and Its Application in Field-Effect Transistors”, Macromolecules. Vol. 40. No 20. pp. 7231-7237.
Reichardt C., T. Welton (1991), “Solvents and Solvent Effects in Organic Chemistry”, VCH, 2nd Ed. P.763.
Šulcová N., Nêmec I., Waisser K., Kies H.L. (1980), “Study of the Electrochemical Oxidation of Phenothiazine Derivatives in Acetonitrile Medium: The Effect of the Structure on the Voltammetric Behavior”, Microchemical Journal. Vol. 25, no. 4. pp. 551-566.
Pluczyk S., Zassowski P., Quinton C., Audebert P., Alain‐Rizzo V., Lapkowski M. (2016), “The influence of the linker on electrochemical and spectroelectrochemical properties of donor-acceptor-donor triphenylamine-s-tetrazine derivatives”, Electrochimica Acta. Vol. 216, no. pp. 160-170.
He Y., Qi Z., Yu J., Wang X., Wie B., Sun Y. (2009), “Synthesis, characterization, and optical properties of a novel alternating 3-dodecyloxythiophene-co-pyridine copolymer”, Polymer Bulletin.Vol. 62. pp. 139-149.
Li K.-C., Hsu Y.-C., Lin J.-T., Yang C.-C., Wei K.-H., Lin H.-C. (2008), “Novel Narrow-Band-Gap Conjugated Copolymers Containing Phenothiazine-Arylcyanovinyl Units for Organic Photovoltaic Cell Applications”, Journal of Polymer Science: Part A: Polymer Chemistry. 2008. Vol.46, no. 13. pp. 4285-4301