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

doi:10.1055/s-0037-1611085

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1399-1407
DOI: 10.1055/s-0037-1611085

paper

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

Abstract

All articles of this category

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.

Key words

3-substituted perylenes - electron donors - Ziegler–Natta catalysts - emission spectra - fluorescence spectra

Full Text

References

References
1 Ziegler K, Breil H, Holzkamp E, Martin H. DE Patent 973626, 1953
2 Natta G, Mazzanti G, Boschi G. DE Patent 1293453, 1956
3 Polyolefins: 50 years after Ziegler and Natta I, Polyethylene and Polypropylene. Kaminsky W. Springer; Berlin: 2013: 37
4 Albizzati E, Giannini U, Collina G, Noristi L, Resconi L. In Polypropylene Handbook. Moore EP. Hanser; Munich: 1996
5 Severn JR, Chadwick JC. Tailor-Made Polymers. Via Immobilization of Alpha-Olefin Polymerization Catalysts. Wiley-VCH; Weinheim: 2008
6 D’Anna V, Norsic S, Gajan D, Sanders K, Pell AJ, Lesage A, Monteil V, Coperet C, Pintacuda G, Sautet P. J. Phys. Chem. C 2016; 120: 18075
7 Kissin YV, Marin VP, Nelson PJ. J. Polym. Sci., Part A: Polym. Chem. 2017; 55: 3832
8 Redzic E, Garoff T, Mardare CC, List M, Hesser G, Mayrhofer L, Hassel AV, Paulik C. Iran Polym. J. 2016; 25: 321
9 Groppo E, Gallo E, Seenivasan K, Lomachenko KA, Sommazzi A, Bordiga S, Glatzel P, Silfhout R, Kachatkou A, Bras W, Lamberti C. ChemCatChem 2015; 7: 1432
10 Nietzel S, Joe D, Krumpfer JW, Schellenberger F, Alsaygh AA, Fink G, Klapper M, Müllen K. J. Polym. Sci., Part A: Polym. Chem. 2015; 53: 15
11 Jang Y, Naundorf C, Klapper M, Müllen K. Macromol. Chem. Phys. 2005; 206: 2027
12 Settels V, Schubert A, Tafipolski M, Liu W, Stehr V, Topczak AK, Pflaum J, Deibel C, Fink RF, Engel V, Engels B. J. Am. Chem. Soc. 2014; 136: 9327
13 Li G, Zhao Y, Li J, Cao J, Zhu J, Sun XW, Zhang Q. J. Org. Chem. 2015; 80: 196
14 Qiao Y, Chen J, Yi X, Duan W, Gao B, Wu Y. Tetrahedron Lett. 2015; 56: 2749
15 Stork M, Herrmann A, Nemnich T, Klapper M, Müllen K. Angew. Chem. Int. Ed. 2000; 39: 4367; Angew. Chem. 2000, 112, 4544
16 Maeda H, Nanai Y, Mizuno K, Chiba J, Takeshima S, Inouye M. J. Org. Chem. 2007; 72: 8990
17 Okamoto S, Kojiyama K, Tsujioka H, Sudo A. Chem. Commun. 2016; 52: 11339
18 Karikachery AR, Lee HB, Masjedi M, Ross A, Moody MA, Cai X, Chui M, Hoff CD, Sharp PR. Inorg. Chem. 2013; 52: 4113
19 Kodama K, Kobayashi A, Hirose T. Tetrahedron Lett. 2013; 54: 5514
20 Ghosh S, Li X, Stepanenko V, Würthner F. Chem. Eur. J. 2008; 14: 11343
21 Suzuki N, Fujita T, Amsharov KY, Ichikawa J. Chem. Commun. 2016; 52: 12948
22 Norman MH, Kelley JL, Hollingsworth EB. J. Med. Chem. 1993; 36: 3417
23 Hisamatsu Y, Aihara H. Chem. Commun. 2010; 46: 4902
24 Pschirer NG, Kohl C, Nolde F, Qu J, Müllen K. Angew. Chem. Int. Ed. 2006; 45: 1401
25 Sato Y, Moriguchi T, Shinozuka K. Chem. Lett. 2012; 41: 420
26 Metal-Catalyzed Cross-Coupling Reactions and More. de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014
27 Nagai Y. Org. Prep. Proced. Int. 1980; 12: 13

Supplementary Material

Supporting Information