Driving the Emission Towards Blue by Controlling the HOMO‐LUMO Energy Gap in BF2‐functionalized 2‐(imidazo[1,5‐a]pyridin‐3‐yl)phenols

Colombo, Gioele; Ardizzoia, G. Attilio; Furrer, Julien; Therrien, Bruno; Brenna, Stefano (2021). Driving the Emission Towards Blue by Controlling the HOMO‐LUMO Energy Gap in BF2‐functionalized 2‐(imidazo[1,5‐a]pyridin‐3‐yl)phenols. Chemistry - a European journal, 27(48), pp. 12380-12387. Wiley-VCH 10.1002/chem.202101520

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Several boron compounds with 2-(imidazo[1,5- a ]pyridin-3-yl)phenols, differentiated by the nature of the substituent (R) in the para position of the hydroxy group, have been synthesized and thoroughly characterized both in solution ( 1 H, 13 C, 11 B, 19 F NMR) and in the solid state (X-ray). All derivatives displayed attractive photophysical properties like very high Stokes shift, high fluorescence quantum yields and a good photostability in solution. Time-Dependent Density Functional Theory (TD-DFT) calculations allowed to define the main electronic transitions as intra ligand transitions ( 1 ILT), which was corroborated by the Natural Transition Orbitals (NTOs) shapes. The homo-lumo energy gap was correlated to the electronic properties of the substituent R on the phenolic ring, as quantified by its σ p Hammett constant.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Furrer, Julien

Subjects:

500 Science > 540 Chemistry

ISSN:

0947-6539

Publisher:

Wiley-VCH

Language:

English

Submitter:

Julien Henri Lucien Furrer

Date Deposited:

25 Jun 2021 13:44

Last Modified:

28 Aug 2021 01:33

Publisher DOI:

10.1002/chem.202101520

PubMed ID:

34160858

BORIS DOI:

10.48350/157142

URI:

https://boris.unibe.ch/id/eprint/157142

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