Synthesis 2019; 51(06): 1399-1407
DOI: 10.1055/s-0037-1611085
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Perylene-Tagged Internal and External Electron Donors for Magnesium Dichloride Supported Ziegler–Natta Catalysts

Bogdan A. Guzeev
,
Dmitry Y. Mladentsev
,
Mikhail I. Sharikov
,
Georgy P. Goryunov
,
Dmitry V. Uborsky
,
Alexander Z. Voskoboynikov*
Department of Chemistry, Lomonosov Moscow State University, 1/3 Leninskie Gory, GSP-1, 119991 Moscow, Russian Federation   Email: voskoboy@med.chem.msu.ru
› Author Affiliations
Further Information

Publication History

Received: 27 August 2018

Accepted after revision: 08 October 2018

Publication Date:
06 November 2018 (eFirst)

Abstract

We report on the synthesis of three perylene-tagged electron donors representing three major types – phthalates, diethers, and alkoxysilanes – which are of importance for the subsequent studies of MgCl2-supported Ziegler–Natta catalysts by means of laser scanning confocal fluorescence microscopy. The obtained products were unambiguously characterized, including by X-ray crystal structure analysis; their photophysical properties (absorption and emission spectra) were investigated as well. Additionally, a reliable and convenient protocol for the multigram synthesis of the required starting material – 3-bromo­perylene (PerBr) – was developed. The key step of this method was synthesis of trialkylsilyl-substituted perylenes, which were further separated by means of flash chromatography followed by conversion of the isolated 3-trialkylsilyl-substituted product to PerBr.

Supporting Information

 
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