Preparation, Structure, Reactivity, Lewis Acidic and Fluorescence Properties of Arylpyridine Based Boron C,N‐Chelates Featuring Weakly Coordinating Anions
Herein, we present the preparation of a series of electronically and/or sterically distinct borenium-type species based on a simple 2-arylpyridine scaffold. Corresponding arylpyridine was firstly subjected to electrophilic borylation (BBr<sub>3</sub>/i-Pr<sub>2</sub>NEt) and formed BBr<sub>2</sub> chelate was reduced with LiAlH<sub>4</sub> to yield arylpyridine boron dihydride. Elimination of one hydride led to Lewis acidic borenium-like products. Four methods of hydride elimination were evaluated and influence of counterions on reactivity, Lewis acidic and luminescent properties was assessed both experimentally and computationally. Arylpyridine chelates featuring weakly coordinating counterions exhibit fluorescent properties upon UV irradiation. Several general trends were inferred to modulate emission wavelength and fluorescence quantum yield. Based on our observations, we have devised and prepared borenium-type fluorophores with yellow-green fluorescence and quantum yields up to 93 %.
Authors
- Karel Škoch (ORCID: https://orcid.org/0000-0001-6406-989X)
- Miroslava Litecká (ORCID: https://orcid.org/0000-0002-5336-9819)
- Kaplan Kirakci (ORCID: https://orcid.org/0000-0002-1068-5133)
- Kamil Lang (ORCID: https://orcid.org/0000-0002-4151-8805)
- Dráhomír Hnyk (ORCID: https://orcid.org/0000-0001-8094-7509)
- Matouš Kloda (ORCID: https://orcid.org/0000-0002-6671-9566)
- Michaela Buziková
Institutions
- Czech Academy of Sciences, Institute of Inorganic Chemistry (CZ)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-10-07
- DOI
- https://doi.org/10.1002/chem.202403263
- Citations
- 7
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- Ministerstvo Školství, Mládeže a Tělovýchovy
- Grantová Agentura České Republiky