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- Title
Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes.
- Authors
Tseng, Sheng‐Ming; Chao, Chi‐Min; Chang, Kai‐Hsin; Wen, Chi‐Sheng; Chou, Tai‐Che; Tsai, Tsung‐Lun; Wu, Ting‐Wen; Haung, Xiao‐Ci; Liu, Jun‐Qi; Hung, Cheng‐Hsien; Liu, Kuan‐Miao; Chou, Pi‐Tai
- Abstract
A series of new six (anilido)‐five (thiazole) membered ring boron difluoride dyes, namely BFs, have been synthesized from the corresponding para‐ and meta‐substituted 2‐(2'‐methylaminophenyl) benzothiazoles through complexation with boron trifluoride. Depending on the substituent effect, the derivatives can switch the emission properties from fluorescence with 100 % emission yield to slim fluorescence but >90 % triplet state population and peak wavelength tuning from 490 nm to 610 nm. Compared with non‐complexed precursors, the rigid, highly planar structure and significantly red‐shifted absorption and emission for BFs indicate that the boron center facilitates the formation of a bridge leading to increased rigidity, and is also involved in π‐conjugation, increasing the transition dipole and suppressing the non‐radiative internal conversion. Together with optical ∼100 % transparent window around 325–375 nm, BFs may find unique applications, among which the fluorescence up‐conversion via triplet‐triplet annihilation is demonstrated.
- Subjects
BORON; BORON trifluoride; FLUORESCENCE yield; DYES &; dyeing; FLUORESCENCE
- Publication
ChemPhotoChem, 2022, Vol 6, Issue 1, p1
- ISSN
2367-0932
- Publication type
Article
- DOI
10.1002/cptc.202100188