DOI: https://doi.org/10.18524/2304-0947.2020.2(74).204385

МЕТОДИ ОТРИМАННЯ, ВЛАСТИВОСТІ ТА ЗАСТОСУВАННЯ ПРОДУКТІВ ВЗАЄМОДІЇ НАФТАЛЕВИХ АНГІДРИДІВ З 1,2-ДІАМІНАМИ (ОГЛЯД)

N. F. Fed’ko

Анотація


Систематизовані літературні дані про методи отримання та спектральні властивості продуктів циклоконденсації нафталевих ангідридів з ароматичними та аліфатичними 1,2-діамінами та про їх застосування як люмінесцентних матеріалів.

Ключові слова


1,8-нафтоїлен-1’,2’-бензімідазол; нафталевий ангідрид; о-фенілендіамін; люмінесценція

Повний текст:

PDF

Посилання


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Пристатейна бібліографія ГОСТ


1. Афанасиади Л.М., Красовицкий Б.М. Моно- и бифлуорофоры. – Х.: ВНИИ монокристалов, 2002. – 448 с.

2. Qian X., Zhenghua Z., Chen K., Yin Q., Zhu G. Photoelectric sensitizing effects of 1,8-naphthalimides and 7H-benzimidazo[2,1-a]benz[d,e]isoquinolin-7-ones derivatives on ZnO // Mater. Chem. Phys. – 1989. – N 23. – P.335-339. https://doi.org/10.1016/0254-0584(89)90076-X.

3. Strzelczyk R, Podsiadly R. Naphthoylenebenzimidazolone dyes as one-component photoinitiators // Coloration Technol. – 2017. – Vol. 133, N 2. – P. 178-183. https://doi.org/10.1111/cote.12266.

4. Patent CN 107652286 A three-aryl amine derivatives and organic light-emitting device. Hui C., Chunxue H., Hai C. Publ. 2.02.2018.

5. Georgiev N., Lyulev M., Alamry K.A., El-Daly S.A., Taib L.A., Bojinov V.B. Synthesis, sensor activity, and logic behavior of a highly water-soluble 9,10-dihydro-7H-imidazo[1,2-b]benz[d,e]isoqionolin-7-one dicarboxylic acid // J. Photochem. Photobiol., A. – 2015. – Vol. 297. – P. 31-38. https://doi.org/10.1016/j.jphotochem.2014.09.013.

6. Liu Z., Peng C., Lu Z., Yang X., Pei M., Zhang G. A novel fluorescent sensor derived from benzimidazo[2,1-a]benz[de]isoquinoline-7-one-12-carboxylic acid for Cu2+, Cd2+ and PPi // Dyes Pigm. – 2015. – Vol. 123. –P. 85-91. https://doi.org/10.1016/j.dyepig.2015.07.027.

7. Patent US 106728 Methods and compositions for treating beta-thalassemia and sickle cell disease. Shen C.;Chou Y., Su T. Publ. 21.04.2016.

8. Bistrzycki A., Risi I. Über die Einwirkung verschiedener Diamine auf Naphtalsäure-anhydrid // Helv. Chim.Acta. – 1925. – Bd.8. – S.810-820.

9. Yarnell J.E., De La Torre P., Castellano F. N. Efficient Phosphorescence from Naphthalenebenzimidizole Coordinated Iridium(III) Chromophores // Eur. J. Inorg. Chem. – 2017. – Vol. 2017, N 44. – P. 5238-5245.https://doi.org/10.1002/ejic.201700669.

10. Zhang K., Dai Y., Zhang X., Xiao Y. Synthesis and photophysical properties of three ladder-type chromophores with large and rigid conjugation structures // Dyes Pigm. – 2014. – Vol. 102. – P. 1-5. https://doi.org/10.1016/j.dyepig.2013.10.030.

11. Hu J., Zhang G., Shih H., Xiaoqing J., Sun P., Cheng C. Synthesis of a highly phosphorescent emitting iridium(III) complex and its application in OLEDs // J. Organomet. Chem. – 2008. – Vol. 693, N 16. – P. 2798-2802. https://doi.org/10.1016/j.jorganchem.2008.05.030.

12. Patent US 284947 Novel color converter. Wagenblast G., Send R., Ivanovici S., Dekeyzer G., Koenemann M.Publ. 29.09.2016.

13. Mamada M., Perez-Bolivar C., Anzenbacher P. Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors // Org. Lett. – 2011. – Vol. 13, N 18. – P. 4882-4885. https://doi.org/10.1021/ ol201973w.

14. Ren W.X., Bhuniya S., Zhang J.F., Lee E.H., Lee S.G., Kim J.S. A new fluorogenic chemodosimetric system for mercury ion recognition // Tetrahedron Lett. – 2010. – Vol. 51, N 44. – P. 5784-5786. https://doi.org/10.1016/j.tetlet.2010.08.088.

15. Claudio-Catalan M.A., Reyes-Gonzalez M.A., Ordonez M. A versatile synthesis of bicyclic lactams from 1,8-naphthalaldehydic acid: an extension of Meyers’ method // Arkivoc. – 2013. – Vol. 2013, N 4. – Р. 413-423. http://dx.doi.org/10.3998/ark.5550190.p008.321.

16. Li D., Zhong Z., Zheng G., Tian Z. A naphthalene benzimidazole-based chemosensor for the colorimetric and on-off fluorescent detection of fluoride ion // Spectrochim. Acta, Part A. – 2017. – Vol. 185. – P. 173-178. https://doi.org/10.1016/j.saa.2017.05.053.

17. Zhou M., Chen J., Liu C., Fu H., Zheng N., Zhang C., Chen Y., Cheng J. Anion binding modes in cis–transisomers of a binding site–fluorophore–π-extended system // Chem. Commun. – 2014. – Vol. 50, N 94. –P. 14748-14751. https://doi.org/10.1039/c4cc07308h.

18. Chen Y., Zhao L., Fu H., Rao C., Li Z., Liu C. Positional isomeric chemosensors: fluorescent and colorimetriccyanide detection based on Si–O cleavage // New J. Chem. – 2017. – Vol. 41, N 17. – P. 8734-8738. https://doi.org/10.1039/C7NJ01633F.

19. Verma M., Luxami V., Paul K. Synthesis, in vitro evaluation and molecular modelling of naphthalimide analogue as anticancer agents // Eur. J. Med. Chem. – 2013. – Vol. 68. – P. 352-360. https://doi.org/10.1016/j.ejmech.2013.07.027.

20. Krasovitskii B. M., Bolotin B.M. Organic luminescent materials. – Manheim. Vch., 1988. – 310 p.

21. Чирва В.Я., Ярмолюк С.М., Толкачова Н.В., Земляков О.Є. Органічна хімія. – Львів: БаК, 2009. – 996 с.

22. Dai M., Zhu W., Xu Y., Qian X., Liu Y., Xiao Y., You Y. Versatile Nitro-Fluorophore as Highly Effective Sensor for Hypoxic Tumor Cells: Design, Imaging and Evaluation // J. Fluoresc. – 2008. – Vol. 28, N 2. – P. 591-597. https://doi.org/10.1007/s10895-007-0303-0.

23. Liu Q., Fang Y., Yi X., Chen R. Synthesis and Metal Ion Probe Properties of Four 1,8-Naphthalimides // Asian J. Chem. – 2013. – Vol. 25, N 6. – P. 3325-3327. https://doi.org/10.14233/ajchem.2013.13649.

24. Vasilev A.A., Baluschev S., Cheshmedzhieva D., Ilieva S., Castano O.D., Vaquero J.J., Angelova S.E., Landfester K. Assembly of New Merocyanine Chromophores with a 1,8-Naphthalimide Core by a New Method for the Synthesis of the Methine Function // Aust. J. Chem. – 2015. – Vol. 68, N 9. – P. 1399-1408. https://doi.org/10.1071/CH15139.

25. Yang H., Lao Y., Chen J., Wu X. Syntheses, Structure and Photoluminescence Properties of Silver(I) Complexes with Naphthalene Iminoimides // Eur. J. Inorg. Chem. – 2009. – № 19. – P. 2817-2824. https://doi.org/10.1002/ejic.200900242.

26. Adib M., Mohammadi B., Ansari S. Bijanzadeh H. Solvent-free reaction between acenaphthoquinone, various benzyls and ammonium acetate: synthesis of 9,10-diaryl-7H-benzo[d,e]imidazo[2,1-a] isoquinolin-7-ones // Tetrahedron Lett. – 2011. – Vol. 52, N 18. – P.2299-2300. https://doi.org/10.1016/j.tetlet.2011.01.091.





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