Solid-state red emission of boron–fluorine complexes with extended π-conjugated structure

Yao, Liang; Dan, Feijun; Liu, Wenjun; Cao, Qiong; Yang, Changying; Zou, Kun; Xiao, Shuzhang

doi:10.1016/j.jfluchem.2013.10.005

Cited by 2 publications

(3 citation statements)

References 59 publications

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“…According to exciton theory, the presence of a bathochromic shift associated with this band suggests the formation of J-aggregates. 61,[66][67][68][69][70] Fig. 4 shows the red shift of the excitation band of the monomer and aggregate spectra.…”

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confidence: 99%

New insight into the photophysics and reactivity of trigonal and tetrahedral arylboron compounds

Santos

Pina

Burrows

et al. 2016

Photochem Photobiol Sci

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The photophysics and reactivity of two tetraphenylborate salts and triphenylborane have been studied using ultrafast transient absorption, steady-state fluorescence, electron paramagnetic resonance with spin trapping, and DFT calculations. The singlet excited state of tetraarylborates exhibit extended π-orbital coupling between two adjacent aryl groups. The maximum fluorescence band, as well as the transient absorption bands centered at 560 nm (τ = 1.05 ns) and 680 nm (τ = 4.35 ns) are influenced by solvent viscosity and polarity, indicative of a twisted intramolecular charge transfer (TICT) state. Orbital contour plots of the HOMO and LUMO orbitals of the tetraarylboron compounds support the existence of electron delocalization between two aryl groups in the LUMO. This TICT-state and aryl-aryl electron extension is not observed for the trigonal arylboron compound, in which excited π-orbital coupling only occurs between the boron atom and one aryl group, which restricts the twist motion of the aryl-boron bond. The excited triplet state is deactivated primarily through aryl-boron bond cleavage, yielding aryl and diphenylboryl radicals. In the presence of oxygen, this photochemistry results in phenoxyl and diphenylboroxyl radicals, as confirmed by EPR spectroscopy of spin trapped radical adducts. The TICT transition and radical generation is not expected for BoDIPY molecules where the rotational vibration of the B-aryl bond is rigid, restricting changes in the geometric structure. In this sense, this work contributes to the development of new BoDIPY derivatives where the TICT transition may be observed for aryl ligands with free rotational vibrations in the BoDIPY structure.

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confidence: 99%

New insight into the photophysics and reactivity of trigonal and tetrahedral arylboron compounds

Santos

Pina

Burrows

et al. 2016

Photochem Photobiol Sci

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“…These BOPIM dyes had high quantum yields and high emission intensities in classical organic solvents. [16] Shen et al analyzed BOPIM-DMA and, it was found that the emission of the molecule changed between pH 2.4-4.0 as "on" and "off" and the pKa was calculated as 3.12. [17] While the interaction of BOPIM-dma with many cations in aqueous systems was examined by Ping et al in 2015, [18] Liu et al in 2017 showed that BOPIM-DMA, an innovative fluorophore, was a sensitive probe for bovine serum albumin (BSA).…”

Section: Introductionmentioning

confidence: 99%

“…got derivatization of BOPIM core again from imidazole side with phenyl and thiophene to expand the π‐conjugation system. These BOPIM dyes had high quantum yields and high emission intensities in classical organic solvents [16] . Shen et al.…”

Section: Introductionmentioning

confidence: 99%

A New Boron 2‐(2′‐pyridyl) Imidazole Complex as a Candidate Photosensitizer for Photodynamic Therapy

Ekmekci

Eris

2022

ChemistrySelect

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In this work, different from the literature, boron 2-(2'-pyridyl) imidazole complex (BOPIM) was derived from pyridine ring side to extend π conjugation for the first time. In addition, the core of BOPIM was brominated to increase the capacity of singlet oxygen generation via intersystem crossing to function as a photosensitizer. According to photophysical measurements, the new BOPIM derivative had comparatively large Stokes shift as 111 nm among boron-fluorine derivatives in the literature. Its singlet oxygen generation potential and toxic effect in the dark were investigated in the presence of singlet oxygen trap 1,3-Diphenylisobenzofuran (DPBF). According to the obtained results, it was seen that the new BOPIM derivative could be a good photosensitizer for photodynamic therapy.

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Solid-state red emission of boron–fluorine complexes with extended π-conjugated structure

Cited by 2 publications

References 59 publications

New insight into the photophysics and reactivity of trigonal and tetrahedral arylboron compounds

New insight into the photophysics and reactivity of trigonal and tetrahedral arylboron compounds

A New Boron 2‐(2′‐pyridyl) Imidazole Complex as a Candidate Photosensitizer for Photodynamic Therapy

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