Benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinines: Synthesis, Structural, and Photophysical Properties

Abstract

A family of highly emissive benzo[4,5]thiazolo[3,2- c][1,3,5,2]oxadiazaborinines, conjugated with the donor 4-dimethylaminophenyl group, was designed and synthesized. Their photophysical, both in solution and in the solid state, and structural properties were investigated. The influence of donor and acceptor substituents (R) in the benzothiazole unit on photophysical properties of complexes was found out. The tetrafluorobenzothiazole analogue exhibits nonbonded nuclear spin-spin coupling between fluorines from the BF group and α-fluorine atom at the benzene ring. Additionally, this boron complex demonstrates a comparatively high solid-state fluorescence quantum yield (Φ = 0.34).

3D Boranil Complexes with Aggregation-Amplified Circularly Polarized Luminescence

“…Moreover, ( R p )/( S p )- 3d and ( R p )/( S p )- 3e , with electron-withdrawing effect of the bromo and nitro groups, respectively, both display distinct red-shifts of λ em around 27 and 65 nm compared with that of ( R p )/( S p )- 3a . The different blue- and red-shifts should be attributed to the different CT processes of ( R p )/( S p )- 3c and the enhanced CT process from ( R p )/( S p )- 3a and ( R p )/( S p )- 3b to ( R p )/( S p )- 3d and ( R p )/( S p )- 3e (Figure S3, S5), respectively . Notably, the different substituent effects of the R group can afford ( R p )/( S p )- 3a – 3e intense fluorescence with λ em at 532–611 nm with Φ f = 1–39%.…”

Ferrocene conjugates linked by 1,2,3‐triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity

“…6‐Chlorobenzothiazole‐2‐amine, [ 35 ] N ‐propargyl‐di(2‐pyridyl)amine ( 1 ), [ 36 ] N , N ‐di(propargyl)aniline ( 2 ), [ 37 ] N , N ‐di(propargyl)benzothiazole‐2‐amine ( 3 ), [ 38 ] azidoferrocene ( 6a ), azidomethylferrocene ( 6b ), 1‐azidoethylferrocene ( 6c ) [ 39 ] and 1,1′‐diazidomethylferrocene ( 7 ) [ 40 ] were prepared according to known procedures.…”

“…6-Chlorobenzothiazole-2-amine, [35] N-propargyl-di (2-pyridyl)amine (1), [36] N,N-di(propargyl)aniline (2), [37] N,N-di(propargyl)benzothiazole-2-amine…”

Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes

“…Recently, we have described a simple synthetic route to highly fluorescent oxadiazaborinine dyes 1 based on electron-rich 1,3-thiazole building blocks ( Figure 1 a), 25 as well as to their benzo[ d ]thiazole analogues. 19b , 26 …”

“…Our conception is based on the incorporation of an electron-rich heterocyclic building block into the oxadiazaborinine structure to increase the chemical stability of these complexes. Recently, we have described a simple synthetic route to highly fluorescent oxadiazaborinine dyes 1 based on electron-rich 1,3-thiazole building blocks (Figure a), as well as to their benzo­[ d ]­thiazole analogues. , …”