Novel pyrromethene dyes with N-ethyl carbazole at the meso position: a comprehensive photophysical, lasing, photostability and TD-DFT study

Thorat, Kishor G.; Kamble, Priyadarshani; Ray, Alok K.; Sekar, Nagaiyan

doi:10.1039/c5cp01741f

Cited by 45 publications

(26 citation statements)

References 63 publications

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“…The minimum energy states for the optimized structures 2–6 were verified by performing frequency calculations on optimized geometries which indicated sum of the imaginary frequencies equal to zero. Using same hybrid functional and basis sets the vertical excitation energies and oscillator strengths were obtained for the 50 lowest S 0 →S n transitions at the optimized S 0 state equilibrium geometries using Time Dependent Density Functional Theory (TD‐DFT) . All the computations in the chloroform media were carried out using the Self‐Consistent Reaction Field (SCRF) under the Polarisable Continuum Model (PCM) , …”

Section: Methodsmentioning

confidence: 99%

Synthesis of Expanded Hetero 2,6‐Pyrihexaphyrins

et al. 2020

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New examples of expanded hetero 2,6‐pyrihexaphyrins 2–6 were synthesized in 12–18 % yields by condensing one equivalent of [10,10'‐bis(p‐tert‐butylphenyl)hydroxymethyl]‐1,3‐bis(2‐thienyl)‐pyridine diol with five different tripyrranes, under mild acid catalyzed conditions. The formation of 2,6‐pyrihexaphyrins 2–6 was confirmed by corresponding molecular ion peak in HR‐MS and were thoroughly characterized by 1D and 2D NMR spectroscopy, absorption, electrochemical and DFT/TD‐DFT studies. In 1H NMR, the proton resonances were either upfield or downfield shifted as the nature of one of the core heterocycles was varied from pyrrole to furan, thiophene, selenophene, and tellurophene indicating that the electronic properties of the macrocycle were altered by changing the core heterocycle. The NMR studies indicated that the macrocycles were nonaromatic in nature and absorption spectra of 2,6‐pyrihexaphyrins 2–6 showed one broad absorption band in the region of 600–1000 nm and two relatively sharp bands in the region of 350–500 nm. The aza analogue 2 showed considerable red shift in the absorption bands compared to other hetero 2,6‐pyrihexaphyrins 3–6. Upon protonation of the macrocycles, the resulting protonated macrocycles 2.H22+‐6.H22+ exhibits bathochromically shifted absorption bands. The redox studies indicated that the 2,6‐pyrihexaphyrins 2–6 are electron deficient and DFT studies supported the distortion and nonaromatic nature of the macrocycles.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Expanded Hetero 2,6‐Pyrihexaphyrins

et al. 2020

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“…The frequencies for 13 4 ] was used as an internal standard for 1 H and 13 C NMR, tetrafluorotoluene and boric acid as external standards for 19 F NMR and 11 B NMR, respectively. All other chemicals used for the synthesis were reagent grade unless otherwise specified.…”

Section: Methodsmentioning

confidence: 99%

“…A representative cyclic voltammogram of the compound 1 is presented in Figure 4 and the relevant data of all compounds 1-5 are included in Table 1. Thus, all compounds 1-5 exhibited redox behaviour of both dithiahomoporphyrin [5] and BODIPY [13] moieties with slight changes in their redox potentials indicating that both dithiahomoporphyrin and BODIPY moieties retain their redox features in compounds 1-5. For example, the compound 1 showed three quasi-reversible/reversible reductions at -0.65 V, -1.01 V and -1.41 V and reversible oxidations at 0.59 V and 0.86 V. In this, the redox waves at 0.59 V and -0.65 V were due to BODIPY unit, whereas redox waves at 0.86 V, -1.01 V and -1.41 V corresponds to the dithiahomoporphyrin moiety.…”

Section: Optical and Electrochemical Propertiesmentioning

confidence: 96%

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Covalently Linked meso‐BODIPYnyl Dithiahomoporphyrins: Synthesis and Properties

et al. 2018

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A series of novel covalently linked meso‐BODIPYnyl dithiahomoporphyrins was synthesized by treating readily available tetrapyrrane and appropriate formyl BODIPY derivatives in the presence of catalytic amount of BF3·OEt2 in CH2Cl2 followed by oxidation using DDQ. The meso‐BODIPYnyl dithiahomoporphyrins were characterized by HR‐MS, 1D, 2D NMR and absorption spectroscopy, cyclic voltammetry and DFT studies. The spectral and electrochemical studies suggest that the BODIPY and homoporphyrin units in meso‐BODIPYnyl dithiahomoporphyrins retain their original identities. The compounds were non‐fluorescent due to intramolecular charge transfer from dithiahomoporphyrin moiety to a respective BODIPY unit in meso‐BODIPYnyl dithiahomoporphyrins. The DFT studies supported the intramolecular charge transfer between the two chromophores in meso‐BODIPYnyl dithiahomoporphyrins.

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“…Due to increase in π – conjugation the energy gap between the HOMO and LUMO of these molecules is reduced which leads to longer absorption and hence emission wavelengths . With varying donor/acceptors the relationship between their photophysical and chemical properties can be very well tuned …”

Section: Introductionmentioning

confidence: 99%

Coumarin‐Rhodamine Hybrids – Synthesis, Photophysical Properties, NLO Properties and DFT Studies

Shreykar

Sekar

2017

ChemistrySelect

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Solvatochromic and solvatofluoric behaviour of three coumarin rhodamine hybrid dyes (Cou‐Rhod1, Cou‐Rhod2 and Cou‐Rhod3) have been studied in ten different solvents with varying polarity. The pH (1‐10) study was done to investigate the spirocyclic ring opening. All the dyes show charge transfer phenomenon in local as well as charge transfer excitation. The non‐linear optical properties of coumarin rhodamine hybrid dyes were studied using solvatochromic method (highest value of αCT for Cou‐Rhod1=2.44 X 10−23; highest value of βCT for Cou‐Rhod2=0.14 X 10−28 and the highest value of γ for Cou‐Rhod2=0.02 X 10−34) and computational (highest value of α0 for Cou‐Rhod3=9.89 X 10−23; highest value of β0 for Cou‐Rhod1=0.90 X 10−28 and highest value of γ for Cou‐Rhod3=5.10 X 10−34) approach. As the non‐radiative rate constant increases quantum yield of the dyes decreases. Correlation of calculated radiative lifetime (τ), radiative (Kr) and non‐radiative rate constant (Knr) has been made to explain the quantum yield of dyes using Strickler‐Berg equation. The charge transfer behaviour, structural parameters and non‐linear optical properties of the dyes are well described by DFT and TD‐DFT calculations.

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Novel pyrromethene dyes with N-ethyl carbazole at the meso position: a comprehensive photophysical, lasing, photostability and TD-DFT study

Cited by 45 publications

References 63 publications

Synthesis of Expanded Hetero 2,6‐Pyrihexaphyrins

Synthesis of Expanded Hetero 2,6‐Pyrihexaphyrins

Covalently Linked meso‐BODIPYnyl Dithiahomoporphyrins: Synthesis and Properties

Coumarin‐Rhodamine Hybrids – Synthesis, Photophysical Properties, NLO Properties and DFT Studies

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