Dataset Information

Driving the Emission Towards Blue by Controlling the HOMO-LUMO Energy Gap in BF₂ -Functionalized 2-(Imidazo[1,5-a]pyridin-3-yl)phenols.

ABSTRACT: 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.

SUBMITTER: Colombo G

PROVIDER: S-EPMC8456857 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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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 G Attilio Ardizzoia G G Furrer Julien J Therrien Bruno B Brenna Stefano S

Chemistry (Weinheim an der Bergstrasse, Germany) 20210712 48

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. Ti ...[more]

PMID: 34160858

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Project description:Optoelectronics usually deals with the fabrication of devices that can interconvert light and electrical energy using semiconductors. The modification of electronic properties is crucial in the field of optoelectronics. The tuning of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and their energy gaps is of paramount interest in this domain. Herein, three nano-Saturn supramolecular complex systems are designed, i.e., Al12N12@S-belt, Mg12O12@S-belt, and B12P12@S-belt, using S-belt as the host and Al12N12, Mg12O12, and B12P12 nanocages as guests. The high interaction energies ranging from -22.03 to -63.64 kcal mol-1 for the complexes demonstrate the stability of these host-guest complexes. Frontier molecular orbital (FMO) analysis shows that the HOMO of the complexes originates from the HOMO of the host, and the LUMO of the complexes originate entirely from the LUMO of the guests. The partial density of states (PDOS) analysis is in corroboration with FMO, which provides graphical illustration of the origin of HOMO and LUMO levels and the energy gaps. The shift in the electron density upon complexation is demonstrated by the natural bond orbital (NBO) charge analysis. For the Al12N12@S-belt and B12P12@S-belt complexes, the direction of electron density shift is towards the guest species, as indicated by the overall negative charge on encapsulated Al12N12 and B12P12. For the Mg12O12@S-belt complex, the overall NBO charge is positive, elaborating the direction of overall shift of electronic density towards the S-belt. Electron density difference (EDD) analysis verifies and corroborates with these findings. Noncovalent interaction index (NCI) and quantum theory of atoms in molecules (QTAIM) analyses signify that the complexes are stabilized via van der Waals interactions. Absorption analysis explains that all the complexes absorb in the ultraviolet (UV) region. Overall, this study explains the formation of stable host-guest supramolecular nano-Saturn complexes along with the controlled tuning of HOMO and LUMO levels over the host and guests, respectively.

Dataset Information

Driving the Emission Towards Blue by Controlling the HOMO-LUMO Energy Gap in BF₂ -Functionalized 2-(Imidazo[1,5-a]pyridin-3-yl)phenols.

Publications

Driving the Emission Towards Blue by Controlling the HOMO-LUMO Energy Gap in BF<sub>2</sub> -Functionalized 2-(Imidazo[1,5-a]pyridin-3-yl)phenols.

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