Cyclotribromoveratrylene in synthesis of porphyrin-containing polyphenols
- Authors: Vainer A.Y.1, Dymaev K.M.1, Kovalenko A.M.1, Barannik N.V.1, Dragunskaya R.M.1, Kotov S.V.1, Pribysh Y.M.1
- 
							Affiliations: 
							- All-Russian Research Institute of Medicinal and Aromatic Plants
 
- Issue: Vol 486, No 2 (2019)
- Pages: 184-188
- Section: Chemistry
- URL: https://journals.eco-vector.com/0869-5652/article/view/13418
- DOI: https://doi.org/10.31857/S0869-56524862184-188
- ID: 13418
Cite item
Abstract
In this work we described a method of synthesis of porphyrin-containing polyphenols. These compounds were chemically combined with the molecular platform which based on cyclotriveratrylene core. The targeted ring system was synthesized through a palladium-catalyzed Suzuki-Miyaura coupling, with cyclotribromoveratrylene and 4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N,N-diporphyrinaniline as a key intermediates. The subsequent chemical transformations of a mentioned system were made for formation of targeted ring compound with free phenolic groups. These functional moieties were partially protected with acid-labile groups. Additionally, the using of porphyrin-containing polyphenols for chemically amplified positive photoresists could produce topological structures with 16 nm resolution on exposure by 13,5 nm wavelength of light.
Keywords
About the authors
A. Ya. Vainer
All-Russian Research Institute of Medicinal and Aromatic Plants
							Author for correspondence.
							Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
K. M. Dymaev
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                								
Corresponding Member of the Russian Academy of Sciences
Russian Federation, 7, Grina street, Moscow, 117216A. M. Kovalenko
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
N. V. Barannik
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
R. M. Dragunskaya
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
S. V. Kotov
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
Yа. M. Pribysh
All-Russian Research Institute of Medicinal and Aromatic Plants
														Email: nvbarannik@mail.ru
				                					                																			                												                	Russian Federation, 							 7, Grina street, Moscow, 117216 						
References
- Collet A. // Tetrahedron. 1987. V. 43. № 24. P. 5725-5739.
- Rao M.L.N., Talode J.B. // Asian. J. Org. Chem. 2016. V. 5. № 1. P. 98-106.
- Milanole G., Gao B., Mari E., et al. // Eur. J. Org. Chem. 2017. № 47. P. 7091-7100.
- Hardie M.J. // Chem. Soc. Rev. 2010. V. 39. № 2. P. 516-527.
- Peyrard L., Dumartin M. - L., Chierici S., et al. // J. Org. Chem. 2012. V. 77. № 16. P. 7023-7027.
- Deschamps J., Langlois A., Martin G., et al. // Inorg. Chem. 2016. V. 55. № 18. P. 9230-9239.
- Combaut G., Chantraine J.-M., Teste J., Glombitza K.-W. // Phytochemistry. 1978. V. 17. № 10. P. 1791-1792.
- Sonntag M., Kreger K., Hanft D., Strohriegl P. // Chem. Mater. 2005. V. 17. № 11. P. 3031-3039.
- Вайнер А.Я., Дюмаев К.М., Коваленко А.М., Бельский Т.Д., Кричевская С.А., Мартова Л.И. // ДАН. 2016. Т. 469. № 5. С. 577-581.
- Xiao S., Li Y.-L., Li Y.-J., et al. // J. Phys. Chem. B. 2004. V. 108. № 43. P. 16 677-16 685.
- Ishiyama T., Murata M., Miyaura N. // J. Org. Chem. 1995. V. 60. № 23. P. 7508-7150.
- Wei B.-G., Chen J., Huang P.-Q. // Tetrahedron. 2006. V. 62. № 1. P. 190-198.
- Goff D.A., Harris R.N., Bottaro J.G., Bedford C.D. // J. Org. Chem. 1986. V. 51. № 24. P. 4711-4714.
- Prakash G.K.S., Reddy V.P., Rasul G., et al. // J. Amer. Chem. Soc. 1998. V. 120. № 51. P. 13 362-13 365.
- Gassman P.G., OReilly N.J. // Tetrahedron Lett. 1985. V. 26. № 43. P. 5243-5246.
Supplementary files
 
				
			 
					 
						 
									
 
  
  
  Email this article
			Email this article 

 Open Access
		                                Open Access Access granted
						Access granted Subscription Access
		                                		                                        Subscription Access
		                                					