Substituent effects on the photophysical properties of fluorescent 2-benzoylmethylenequinoline difluoroboranes: A combined experimental and quantum chemical study

Zakrzewska, Anna; Zaleśny, Robert; Kolehmainen, Erkki; Ośmiałowski, Borys; Jędrzejewska, Beata; Ågren, Hans; Pietrzak, Marek

doi:10.1016/j.dyepig.2013.08.002

Cited by 49 publications

(62 citation statements)

References 82 publications

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“…This is well illustrated in Fig. 5 Despite the systematic overestimation of the transition energy, it has been shown that TD-DFT allows reproduction of the band shapes of both the absorption and emission of fluoroborates with good to excellent accuracy [34,35,47,88,89,120]. In other words, the PES provided by TD-DFT are reasonably accurate for this class of dyes.…”

Section: Fluoroborate Derivativesmentioning

confidence: 73%

Computational Molecular Electronic Spectroscopy with TD-DFT

Jacquemin

Adamo

2015

Topics in Current Chemistry

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In this chapter we present applications of TD-DFT aiming at reproducing and rationalizing the optical signatures of molecules, and, more precisely, the absorption and fluorescence spectra of conjugated compounds belonging to both organic and inorganic families. We particularly focus on the computations going beyond the vertical approximation, i.e., on the calculation of 0-0 energies and vibronic spectra with TD-DFT, and on large applications performed for "real-life" structures (organic and inorganic dyes, optimization of charge-transfer structures, rationalization of excited-state proton transfer, etc.). We present a series of recent applications of TD-DFT methodology for these different aspects. The main conclusions of TD-DFT benchmarks aiming at pinpointing the most suited exchange-correlation functionals are also discussed.

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Section: Fluoroborate Derivativesmentioning

confidence: 73%

Computational Molecular Electronic Spectroscopy with TD-DFT

Jacquemin

Adamo

2015

Topics in Current Chemistry

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“…Furthermore, it was implied that the nitrogen atom could contribute to suppressing ACQ by partially disordering π‐stacking at the boron complex moiety. Based on these results, we designed ketoiminate complexes by employing fused structures in order to realize constant emission efficiencies in the solid state, such as the amorphous and crystal forms, as well as in solution. By introducing the fused structure at the nitrogen atom in the ketoiminate ligand, molecular motions should be effectively suppressed.…”

Section: Resultsmentioning

confidence: 99%

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

2017

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Mechanochromic luminescent molecules often suffer from critical loss of luminescence intensity during phase transitions in the solid state. In this study, we present mechanochromic luminescent molecules that can provide clear color changes with constant emission intensity during phase transitions. It was reported that the class of aggregation‐induced emission (AIE)‐active boron complexes can present intense emission by freezing intramolecular motions. According to this mechanism, we designed a complex with a fused ligand to preserve the enhanced emission in the aggregated state in the AIE during phase transitions between the solution, amorphous, and crystalline states. From optical measurements, it was shown that the synthesized boron complexes present bright emission in various phases. In particular, as we expected, the luminescence color was clearly altered during phase transition, whereas the emission intensity changed only slightly. Finally, we also found that diverse luminescence colors were obtained from each polymorph and for various substituents as induced by the substituent effect. The results in the series of mechanistic studies show that electronic interactions and π–π interactions can modulate the electronic conjugation system of the complexes without causing loss of emission efficiency.

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“…Another examples are b-diketonate (OBF 2 O) and b-ketoiminate (NBF 2 O) difluoroboranyls [13]. Their easy functionalization makes the dyes very attractive as immobilized [13] probes or indicators [2,14], as dyes for biolabelling [15], chemodosimeters [16]. They also are used in solar cells applications [17].…”

Section: Introductionmentioning

confidence: 99%

“…They are usually characterized by: (a) high extinction coefficient, (b) high fluorescence quantum yield, (c) narrow emission band, (d) relatively long excited-state lifetime, (e) great photostability and (f) large two-photon absorption cross-section [1][2][3]. The photophysical and photochemical properties of the fluorescent difluoroboranyl dyes can be easily modified, e.g.…”

Section: Introductionmentioning

confidence: 99%

“…The photophysical and photochemical properties of the fluorescent difluoroboranyl dyes can be easily modified, e.g. by an introduction of the suitable substituent [2], by Electronic supplementary material The online version of this article (doi:10.1007/s00289-017-2201-1) contains supplementary material, which is available to authorized users.…”

Section: Introductionmentioning

confidence: 99%

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Difluoroboranyl derivatives as efficient panchromatic photoinitiators in radical polymerization reactions

Jędrzejewska

Ośmiałowski

2017

Polym. Bull.

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Photoinitiating systems based on BF 2 derivatives and tetramethylammonium phenyltriethylborate salt were tested in photopolymerization reactions through the photo-DSC method. The good rates of TMPTA polymerization and final monomer conversion were obtained for tested system. The effect of the type of heterocycle on their properties was revealed. The excited state processes, investigated by nanosecond flash photolysis, lie on a fast excited state photoinitiated cleavage leading to reactive species. A triplet state is observed for investigated derivatives.

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Substituent effects on the photophysical properties of fluorescent 2-benzoylmethylenequinoline difluoroboranes: A combined experimental and quantum chemical study

Cited by 49 publications

References 82 publications

Computational Molecular Electronic Spectroscopy with TD-DFT

Computational Molecular Electronic Spectroscopy with TD-DFT

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

Difluoroboranyl derivatives as efficient panchromatic photoinitiators in radical polymerization reactions

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