Cyano-rich donor-acceptor-donor-type NLOphores containing dialkylated triazene and aniline groups

Mammadova, Flora; Inyurt, Fevzi Can; Barsella, Alberto; Dengiz, Çağatay

doi:10.1016/j.dyepig.2022.110894

Cited by 10 publications

(28 citation statements)

References 70 publications

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“…Paper / PSP Template for SynOpen Thieme previous work. 11 In summary, the synthesis of 5 different electron-rich alkynes 1a-e was performed using Sonogashira cross-coupling reactions. With substrates 1a-e in hand, subsequent click-type [2+2] cycloaddition reactions were tested.…”

Section: Synopenmentioning

confidence: 99%

“…Compounds 1a-e were prepared according to literature procedures. 11 Solvents for extraction or column chromatography were distilled before usage. Reactions under exclusion of air or water were performed in oven-dried glassware and under argon or N2 atmosphere.…”

Section: Template For Synopen Thiemementioning

confidence: 99%

“…Push–pull systems also find applications in a wide variety of areas such as organic light-emitting diodes (OLEDs), 8 organic field-effect transistors (OFETs), 9 dye-sensitized solar cells (DSSCs), 10 and nonlinear optical (NLO) devices. 11 In this context, it is essential to develop efficient synthetic strategies to access these valuable targets. All the above-mentioned features make click-type transformations an excellent area to explore.…”

Section: Table 1 Homo/lumo Depictions and Esp Maps For ...mentioning

confidence: 99%

“…4 The excellent optoelectronic properties of these structures explain the growing interest in their synthesis by using short and efficient click-type methods. Push-pull systems also finds applications in a wide variety of high-tech areas such as organic light-emitting diodes (OLEDs), 8 organic field-effect transistors (OFETs), 9 dye-sensitized solar cells (DSSCs), 10 and nonlinear optical (NLO) devices 11 . In this context, it is essential to develop efficient synthetic strategies to access these valuable targets.…”

mentioning

confidence: 99%

“…To circumvent this issue, we have recently designed unsymmetrical dialkylaniline/triazenesubstituted unsymmetrical alkynes that undergo successful [2+2] cycloaddition-retroelectrocyclizations to form πconjugated non-planar push-pull NLOphores. 11 As part of our ongoing investigations on push-pull-type NLOphores, we herein present the synthesis of homoconjugated push-pull chromophores via click-type formal [2+2] cycloaddition.…”

mentioning

confidence: 99%

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Click-Type Synthesis of Homoconjugated Push–Pull Chromophores: Computational Investigation of Optical and Nonlinear Optical (NLO) Properties

Inyurt¹,

Mammadova²,

Dengiz³

2022

SynOpen

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Section: Synopenmentioning

confidence: 99%

Section: Template For Synopen Thiemementioning

confidence: 99%

Section: Table 1 Homo/lumo Depictions and Esp Maps For ...mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Click-Type Synthesis of Homoconjugated Push–Pull Chromophores: Computational Investigation of Optical and Nonlinear Optical (NLO) Properties

Inyurt¹,

Mammadova²,

Dengiz³

2022

SynOpen

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1,3‐Diynes as Precursors for the Synthesis of Triazene‐ and Diethylaniline‐Bearing Push‐Pull NLOphores

Can Inyurt,

Dengiz

2024

ChemistrySelect

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Within the scope of this study, a total of eight new NLOphores of the D‐π‐A‐π‐D type have been synthesized. This was achieved by applying click‐type [2+2] cycloaddition‐retroelectrocyclization reactions of unsymmetrical 1,3‐diynes with well‐known electron‐deficient alkenes, TCNE, and TCNQ. Furthermore, essential insights into the optical properties of the synthesized NLOphores were obtained from comparisons with four model compounds synthesized separately within this study. The thermal stability of the NLOphores was assessed through thermal gravimetric analysis (TGA). NLOphores synthesized using two distinct electron‐deficient alkenes exhibit low energy absorption bands covering most of the visible region with λmax values ranging from 466 nm to 723 nm. Theoretical studies, including time–dependent density functional theory (TD‐DFT) investigations, frontier orbital visualizations, and electrostatic potential maps, have been utilized to further investigate the intramolecular charge transfer properties of chromophores. The NLO responses of the chromophores were determined through DFT calculations. It is worth noting that the average polarizability and first hyperpolarizability values (α(tot)=106.392–159.709×10−24 esu; β(tot)=387.552–417.359×10−30 esu) obtained from these calculations show significant promise compared to literature data.

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Electronically tunable cyanoethynylethenes and Tetracyanobuta-1, 3-dienes based Push–pull organic chromophores for enhanced nonlinear optical Activity: A DFT perspective

Kumar

Yadav

Singh

2023

Computational and Theoretical Chemistry

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Cyano-rich donor-acceptor-donor-type NLOphores containing dialkylated triazene and aniline groups

Cited by 10 publications

References 70 publications

Click-Type Synthesis of Homoconjugated Push–Pull Chromophores: Computational Investigation of Optical and Nonlinear Optical (NLO) Properties

Click-Type Synthesis of Homoconjugated Push–Pull Chromophores: Computational Investigation of Optical and Nonlinear Optical (NLO) Properties

1,3‐Diynes as Precursors for the Synthesis of Triazene‐ and Diethylaniline‐Bearing Push‐Pull NLOphores

Electronically tunable cyanoethynylethenes and Tetracyanobuta-1, 3-dienes based Push–pull organic chromophores for enhanced nonlinear optical Activity: A DFT perspective

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