Aggregation induced emissive carbazole-based push pull NLOphores: Synthesis, photophysical properties and DFT studies

Lanke, Sandip K.; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2015.09.013

Cited by 46 publications

(16 citation statements)

References 59 publications

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“…The dyes 4a–4d show blue shift in absorption (5‐10 nm) and emission (10‐50 nm) from nonpolar to polar solvents (Figures S1 and S2). The ground states of 4a–4d are better stabilized in nonpolar solvents compared with their excited state . This is attributed to the difference in the solvation of ground and first excited states resulting in “hypsochromic shift” in their absorption and emission .…”

Section: Resultsmentioning

confidence: 99%

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Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

Yadav

Taware

Sreenath³

et al. 2020

J of Physical Organic Chem

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To investigate the effect of substituents in azo dyes on their nonlinear optical properties, four azo dyes were synthesized using ethyl‐3‐hydroxy‐2‐naphthoate as a coupler and characterized. The polarizability (α) and hyperpolarizability (β and γ) constants were determined by using solvatochromic and computational method. A group of global hybrid and range seperated hybrid functionals having different Hartree‐Fock exchange percentage were used to evaluate the NLO properties. The functional ωB97 and ωB97XD performed better in the determination of polarizability (α) and hyperpolarizability (β and γ), respectively. The observed results for polarizability and hyperpolarizability parameters were supported by highest occupied molecular orbital‐lowest unoccupied molecular orbital (HOMO‐LUMO) energy gap, Hammett‐coefficient (σ), excited‐state coefficients (σex), and hyper‐hardness (Γ) values. Third‐order NLO properties were analyzed by using Z‐scan technique. The –OCH3 substituted dye 4d shows higher value of molecular susceptibility (χ(3)), polarizability (α), and hyperpolarizability (β and γ) parameters among the studied azo dyes. They are likely to have the potential applications in optoelectronics and photonics.

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Section: Resultsmentioning

confidence: 99%

“…For the synthesis of azo dyes 4a–4d, the required intermediate diazotized aromatic amines 3a–3d were synthesized from reported protocol . While, the intermediate 2 and the dyes 4a – 4d were synthesized from reported strategies Scheme …”

Section: Resultsmentioning

confidence: 99%

Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

Yadav

Taware

Sreenath³

et al. 2020

J of Physical Organic Chem

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“…In the last decades, AIE molecules involving intramolecular restriction [11,12], planarity and rotation ability [13], twisted intramolecular charge transfer (TICT) [14][15][16] have been reported, since the first report of AIE material by Tang and co-workers in 2001 [17]. In recent years, variety of fluorophores have been designed and synthesized with conjugated [18] and twisted skeleton to exhibit AIE [12,19].…”

Section: Introductionmentioning

confidence: 99%

AIE Based Coumarin Chromophore - Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters

Lanke

Sekar

2015

J Fluoresc

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A new class of red emitting extensively conjugated donor-π-acceptor type dyes bearing coumarin units have been synthesized by condensation of 7-(diethylamino)-2-oxo-2 H-chromene-3-carbaldehyde with different active methylenes. All the dyes are characterized by (1)H NMR, (13)C NMR and HRMS spectroscopy. The photophysical behaviour and the relation between structure and properties of the coumarin "push-pull" derivatives were investigated experimentally. The dyes exhibited positive solvatochromism and solvatofluorism in solution of varying polarity. These coumarin dyes show aggregation induced emission properties with red emitting fluorescence. They show absorption in the range of 501-528 and emission in the range of 547-630 nm. We evaluated photophysical properties of coumarin dyes using solvotochromism and solvent dependent shift in the emission wavelength. All the synthesized coumarin dyes COS1-COS4 are showing very good solvatochromic properties.

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“…Recent advancements in aggregation induced emission (AIE) based materials opens up new opportunities for the preparation of organic‐molecule‐based fluorescent nanoprobes . To date, a large number of AIE active molecules with different chemical characteristics have been discovered and utilized for fabrication of AIE‐active FONs including naphthalene‐diimide, tetraphenylethene (TPE), siloles, PEGylated carbazole and some metal complexes . Such probes have been used as fluorescent tools for the detection of biomolecules and biochemical events, imaging agents in live cells, organic light‐emitting devices and chemosensors …”

Section: Introductionmentioning

confidence: 99%

“…[22][23][24][25][26] To date, al arge number of AIE active molecules with different chemical characteristics have been discovered and utilized for fabrication of AIE-active FONs includingn aphthalene-diimide, tetraphenylethene( TPE), siloles, PEGylated carbazole and some metal complexes. [27][28][29][30][31][32] Such probes have been used as fluorescent tools for the detection of biomoleculesa nd biochemical events, imaging agents in live cells, organic light-emitting devices and chemosensors. [33][34][35] AIE active molecules can be transformed into functionalized nanoparticles with ar ange of applicationsi nt he biomedical field.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Dependent Nanostructures Based on Active π‐Aggregation Induced Emission Enhancement of New Carbazole Derivatives of Triphenylacrylonitrile

Maity

Aich

Prodhan

et al. 2019

Chemistry A European J

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In the present study, the carbazole and 2,3,3‐triphenylacrylonitrile (TPAN) nanostructures (2‐CTPAN and 2,2′‐CTPAN) have been designed and synthesized by Pd‐catalyzed Sonogashira cross‐coupling reaction. CTPAN exhibit aggregation‐induced emission enhancement (AIEE) behavior in water with high fluorescence quantum yield. Both the compounds show tunable self‐assembly in water as well as in N,N‐dimethylformamide (DMF) by extended π–π stacking interactions. CTPAN can be self‐assembled into spherical particles in water and the structures of these self‐assemblies have been investigated using X‐ray diffraction. Interestingly, 2‐CTPAN and 2,2′‐CTPAN form organogels with a critical gelation concentration (CGC) of 11 and 15 mg mL−1, respectively, in DMF and exhibit acicular and rod shaped morphology, respectively. The single‐crystal structure of 2‐CTPAN shows that the intermolecular C−H⋅⋅⋅π interactions lock the molecular conformation into a staircase‐shaped supramolecular assembly. These AIEE active compounds reveal high water dispersibility, strong yellow fluorescence with high quantum yield, promising photostability and excellent biocompatibility, which make them potential bioimaging agents.

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Aggregation induced emissive carbazole-based push pull NLOphores: Synthesis, photophysical properties and DFT studies

Cited by 46 publications

References 59 publications

Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

Experimental and theoretical investigation of linear and nonlinear optical properties of ethyl‐3‐hydroxy‐2‐napthoate azo dyes by solvatochromic, computational aspects, and Z‐scan technique

AIE Based Coumarin Chromophore - Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters

Solvent‐Dependent Nanostructures Based on Active π‐Aggregation Induced Emission Enhancement of New Carbazole Derivatives of Triphenylacrylonitrile

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