10, 9-Oxaboraphenanthrenes as luminescent fluorophores. Issue 11 (17th March 2016)

• Record Type: Journal Article
• Authors: Budanow, Alexandra; von Grotthuss, Esther; Bolte, Michael; Wagner, Matthias; Lerner, Hans-Wolfram
• Is Part Of: Tetrahedron. Volume 72:Issue 11(2016)
• Page Start: 1477
• Page End: 1484
• Publication Date: 2016-03-17
• Subjects: Oxaboraphenanthrene -- Fluorophores -- Luminescence -- X-ray structure analysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.01.054
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Reactions of 9-chloro-10, 9-oxaboraphenanthrene (1 ) with the phenyl-, p- tolyl-, m -xylyl-, mesityl-, 2, 4, 6-tri- iso -propylphenyl-, 3, 5-bis(trifluoromethyl)phenyl-, and pentafluorophenyl-Grignard reagents resulted in the formation of the corresponding oxaboraphenanthrene derivatives namely 9-phenyl- (2 ), 9- p- tolyl- (3 ), 9-(3, 5-dimethylphenyl)- (9- m -xylyl-) (4 ), 9-mesityl- (5 ), 9-(2, 4, 6-tri- iso -propylphenyl)- (6 ), 9-(3, 5-bis(trifluoromethyl)phenyl)- (7 ), and 9-(pentafluorophenyl)-10, 9-oxaboraphenanthrene (8 ). 9-Trisyl- (9 ) and 9-supersilyl-10, 9-oxaboraphenanthrene (10 ) were obtained selectively employing1 and Li[C(SiMe3 )3 ] or Na[Si t Bu3 ] as reactants. The compounds4 –9 were characterized by X-ray crystallography. The fluorescence measurements of5 –9 embedded in PMMA show emission bands with λmax from 341 to 373 nm. Graphical abstract: