Donor-Acceptor-Appended Triarylboron Lewis Acids: Ratiometric or Time-Resolved Turn-On Fluorescence Response toward Fluoride Binding
- Authors
- Lee, Heechai; Jana, Saibal; Kim, Juhee; Lee, Sang Uck; Lee, Min Hyung
- Issue Date
- Jan-2020
- Publisher
- American Chemical Society
- Citation
- Inorganic Chemistry, v.59, no.2, pp 1414 - 1423
- Pages
- 10
- Indexed
- SCIE
SCOPUS
- Journal Title
- Inorganic Chemistry
- Volume
- 59
- Number
- 2
- Start Page
- 1414
- End Page
- 1423
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/1344
- DOI
- 10.1021/acs.inorgchem.9b03159
- ISSN
- 0020-1669
1520-510X
- Abstract
- Triarylboron Lewis acid compounds (CzmBoT (1c) and DPAmBoT (2c)), in which carbazole (Cz) or diphenylamine (DPA) donors are linked with a triazine acceptor in the ortho position of the phenylene ring are prepared and characterized. The treatment of 1c and 2c with the fluoride anion produces the corresponding fluoride adducts [1cF](-) and [2cF](-) as a tetraethylammonium salt. An X-ray diffraction study of [1cF](-) reveals a twisted conformation between the Cz and phenylene rings. The Cz-containing 1c shows a ratiometric fluorescence change upon fluoride binding, while the DPA-containing 2c exhibits a turn-on fluorescence response in tetrahydrofuran. In particular, both fluoride adducts exhibit thermally activated delayed fluorescence (TADF) properties with microsecond-range lifetimes. Electrochemical and theoretical analysis suggests that the intramolecular charge-transfer transition from the donor to a conjugated acceptor fragment is switched to the donor to a triazine transition after fluoride binding. Theoretical analysis further demonstrates the twisted structure, effective highest occupied molecular orbital-lowest unoccupied molecular orbital separation, and the small energy splitting between the excited singlet and triplet states for the fluoride adducts, with all supporting the observed TADF. The time-resolved fluorescence measurements of 2c in the presence of both fluoride and a competitive fluorescent dye (Coumarin 6) effectively eliminate the short-lived fluorescence of a dye, retaining long-lived fluorescence signals originating only from [2cF](-).
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