Influence of electron-withdrawing groups in two-photon absorption of imidazopyridines derivatives

Pelosi, André Gasparotto; Cocca, Leandro H.Z.; Abegão, Luis M. G.; Sciuti, Lucas F.; Piguel, Sandrine; Boni, Leonardo De; Mendonça, Cleber Renato

doi:10.1016/j.dyepig.2021.109972

Cited by 18 publications

(9 citation statements)

References 45 publications

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“…Numerous organic materials have already investigated [13][14][15][16][17][18], but the search for novel or modified organic molecular structures with significant NLO responses continues. However, attempting to synthesize a novel molecular structure may be futile and expensive without prior fundamental research and understanding of its inherent optical properties.…”

Section: Introductionmentioning

confidence: 99%

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Araújo,

Rodrigues,

Alencar

et al. 2024

Photonics

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This study investigates the potential of a set of pseudo-stilbene and azobenzene molecular structures to become optical frequency converters for optical communications based on a detailed exploration of the first-order molecular hyperpolarizability (βHRS), which is the microscopic counterpart of second harmonic generation (SHG). βHRS values were obtained via quantum chemical calculations using the Gaussian 16 software package in solvent and gas-phase media at different wavelengths, i.e., 1064 nm, 1310 nm, and 1510 nm. The latter two wavelengths are of particular interest for optical communications. Our study focused on discerning how the molecular structure influences the βHRS response, explicitly highlighting the influence of the azomethine group (CH=N). The results revealed that the molecular planarity, affected by this group, plays a crucial role in modulating the optical properties. The highest βHRS value in a solvent medium using the CAM-B3LYP/6-311+G(2d,p) level of theory achieved in this work was around 1400 ×10−30cm4startvolt−1, four orders of magnitude higher than KDP (0.2 ×10−30cm4startvolt−1), which is a reference in SHG experiments at 1064 nm. The highest calculated βHRS value at the same level of theory and solvent at 1310 nm and 1550 nm was 631 × 10−30cm4startvolt−1 and 456 × 10−30cm4startvolt−1, respectively. All these values belong to molecular structures with azo-coupling with donor (4-NMe2) and acceptor (4′-NO2) peripheral groups, designated as AB-3.

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Section: Introductionmentioning

confidence: 99%

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Araújo,

Rodrigues,

Alencar

et al. 2024

Photonics

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“…In general, D-2PA cross-sections of different systems have been experimentally determined, 23,[47][48][49][50][51][52][53][54] however, ND-2PA remains a relatively uncharted area. [55][56][57] The reported experimental studies investigate D-2PA and ND-2PA spectra, however, the absolute ND-2PA cross-sections of FPs that relate to this study remain unreported.…”

Section: Introductionmentioning

confidence: 99%

Non-Degenerate Two-Photon Absorption of Fluorescent Protein Chromophores

Elayan,

Brown

2023

Preprint

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Two-photon absorption (2PA), where a pair of photons are absorbed simultaneously, is recognized as a potent bioimaging technique, which depends on the quantified 2PA probability, defined as cross-section (σ2PA). The absorbed photons either have equivalent (ω1 = ω2) or different frequencies (ω1 ≠ ω2), where the former is degenerate 2PA (D-2PA) and the latter is non-degenerate 2PA (ND-2PA). ND-2PA is of particular interest since it is a promising imaging technology with flexibility of photon frequencies and enhanced cross-sections, however, it remains a relatively unexplored area compared to D-2PA. This work utilizes time-dependent density functional theory (TD-DFT) and second-order approximate coupled-cluster with the resolution-of identity approximation (RI-CC2), for the excitation from S0 to S1, to investigate σD-2PA and σND-2PA of fluorescent protein chromophore models. Interestingly, comparison of the CAMB3LYP and RI-CC2 computations show a qualitative trend in the computed σND-2PA improvements and vertical excitation energy, ΔE. As expected, the computed values of σND-2PA are quantitatively larger than σD-2PA, where chromophores with the largest values of σD-2PA show greater potential for σND-2PA improvement. Anionic chromophores demonstrated improvements up to 14%, while substantial enhancements were observed in neutral chromophores with some achieving a 30% increase.

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“…Recent studies have shown that chemical modifications of one of the nucleobase cores, the purine heterocycle, by an introduction of electron donor and acceptor fragments, provide highly emissive push–pull-type compounds, whose fluorescence (FL) quantum yield (Φ FL ) can reach unity. − While the fluorescent nature of these compounds limits the potentially attainable efficiency of the corresponding purine-based OLEDs, singlet harvesting compounds still find a practical use in blue light-emitting devices due to the poor chemical stability of the triplet harvesting alternatives . Several early reports of OLEDs showing electroluminescence in the important deep-blue and violet parts of the spectrum have been demonstrated using purine-based emitters. , In addition, it was recently reported that 9-methylpurine-based derivatives containing phenoxazine groups in the para-position of the phenyl substituent at C6 or C2 and C6 positions of purine possess thermally activated delayed fluorescence, further underlining the potential prospects of the compound class for the application in organic electronic devices .…”

Section: Introductionmentioning

confidence: 99%

Photophysical and Electrical Properties of Highly Luminescent 2/6-Triazolyl-Substituted Push–Pull Purines

et al. 2022

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New push–pull N(9)-alkylated 6-piperidino-2-triazolylpurine and 2-piperidino-6-triazolylpurine derivatives are synthesized, and their optical and optoelectronic properties are comprehensively characterized with experimental and computational methods. The compounds possess intense violet or blue fluorescence with fluorescence quantum yields of up to 91% in solution and 40% in host-free films. Depending on their structural composition, the compounds have ionization energy in the range of 5.25–6.04 eV, electron affinity of 2.18–3.15 eV, and triplet energy of 2.52–2.95 eV. Due to the presence of hole-transporting purine and electron-transporting triazole fragments, compounds exhibit bipolar charge-transportation ability. Despite the favorable emissive properties of the studied push–pull purines, their electroluminescence in thin films is quenched owing to large current densities that are present even at a moderate driving voltage. This marks application directions related to a predominantly charge-transportation functionality as the most suitable for this compound class.

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Influence of electron-withdrawing groups in two-photon absorption of imidazopyridines derivatives

Cited by 18 publications

References 45 publications

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Pseudo-Stilbene- and Azobenzene-Type Systems for Optical Frequency Conversion: Estimating the First-Order Molecular Hyperpolarizability

Non-Degenerate Two-Photon Absorption of Fluorescent Protein Chromophores

Photophysical and Electrical Properties of Highly Luminescent 2/6-Triazolyl-Substituted Push–Pull Purines

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