Optoelectronic features of Y-shaped push–pull molecules based on imidazole

Pokładko-Kowar, Monika; Nosidlak, Natalia; Gondek, E.; Kityk, I.V.; Bureš, Filip; Kulhánek, Jiří; Karasiński, Paweł

doi:10.1007/s11082-015-0263-6

Cited by 15 publications

(5 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These two functionals are found to be appropriate for calculating the absorption and fluorescence spectra of p-conjugated organic chromophores [41,42]. For instance, the calculated absorption λabs and emission λflu wavelengths of D3 agree well with the available experimental data [28] (see Tables 4-5). Solvent dielectric effects were considered using the popular implicit conductor-like polarizable continuum model (C-PCM) [43] which has become an increasingly useful tool for predicting the electronic structures of ground and excited states of molecules in solution [44].…”

Section: Computational Detailssupporting

confidence: 63%

“…Compared to D1, the positions of the donor/acceptor groups are inversed in D2. In D3 studied by Pokladko-Kowar et al [28], the ethylenephenyl unit is added to the D1 p-linker. The 3,6-disubstituted2-phenylphenanthro [9,10]imidazole D4 is the planar analogue of D1.…”

Section: Introductionmentioning

confidence: 99%

“…The fluorescence transition energies Eflu, fluorescence wavelengths λflu, main MO assignments, and the oscillator strength f for the lowest singlet excited state are listed in Table6. Pokladko-kowar et al[28] have investigated the fluorescent properties of the commercial dye D3 and its derivatives. The calculated emission λflu wavelength values of D3, 545(557) nm are in good agreement with experimental result, 535 nm.…”

mentioning

confidence: 99%

See 2 more Smart Citations

DFT and TD-DFT study on quadratic NLO response and optoelectronic activity in novel Y-shaped imidazole-based push-pull chromophores

Zaitri

Mekelleche

2021

J Mol Model

View full text Add to dashboard Cite

A theoretical analysis of a series of imidazole-based Y-shaped chromophores, D1-D8, is performed in order to investigate their non(linear) optical, fluorescence, and charge-transport properties. The calculations have been carried out employing DFT and TD-DFT methods at CAM-B3LYP and M06-2X levels of theory. FMO analysis reveals that in ground state, highest occupied molecular orbital is localized on the 4,5-dimethylanilino donor moiety and imidazole core while lowest unoccupied molecular orbital spreads on p-linker and nitro acceptor moieties. Vertical absorption and fluorescence transitions are characterized as intramolecular charge transfer and maximum absorption and fluorescence wavelengths show that by changing the p-bridge to the imidazole C2, we can tune fluorescence color from cyan to orange. Calculated (hyper)polarizabilities show that elongation of πlinker by polarizable subunits, such as double bonds or heteroaromatic rings, increases significantly the nonlinear response and shifts the charge-transfer band bathochromically. Calculated reorganization energies indicate that the studied compounds are hole-transporting materials rather than electron-transporters. Interestingly, D7 and D8, with higher hyperpolarizabilities, are predicted to be potent candidates for NLOdevices while D5 and D8 molecules are expected to be promising candidates for luminescent materials and good hole-transport materials for organic light emitting diodes.

show abstract

Section: Computational Detailssupporting

confidence: 63%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

DFT and TD-DFT study on quadratic NLO response and optoelectronic activity in novel Y-shaped imidazole-based push-pull chromophores

Zaitri

Mekelleche

2021

J Mol Model

View full text Add to dashboard Cite

show abstract

“…On the contrary, imidazole chromophores 49 with two DMA units showed significant light emission as a response to applied electric field, and therefore, were used as promising active materials for OLEDs 91…”

Section: Y‐shaped Moleculesmentioning

confidence: 99%

Alphabet‐Inspired Design of (Hetero)Aromatic Push–Pull Chromophores

Klikar

Solanke

Tydlitát

et al. 2016

The Chemical Record

View full text Add to dashboard Cite

Push-pull molecules represent a unique and fascinating class of organic p-conjugated materials. Herein, we provide a summary of their recent extraordinary design inspired by letters of the alphabet, especially focusing on H-, L-, T-, V-, X-, and Y-shaped molecules. Representative structures from each class were presented and their fundamental properties and prospective applications were discussed. In particular, emphasis is given to molecules recently prepared in our laboratory with T-, X-, and Y-shaped arrangements based on indan-1,3-dione, benzene, pyridine, pyrazine, imidazole, and triphenylamine. These push-pull molecules turned out to be very efficient charge-transfer chromophores with tunable properties suitable for second-order nonlinear optics, two-photon absorption, reversible pH-induced and photochromic switching, photocatalysis, and intercalation.

show abstract

“…Imidazole-centred tripodal molecules have found various applications as pharmacophores, 36 charge-transfer (CT) chromophores, 37 fluorophores, [38][39][40][41][42] molecular sensors capable of detecting various analytes such as F À , BF 4 À /ClO 4 À , Hg 2+ , Zn 2+ , cysteine or picric acid, [43][44][45][46][47][48][49][50][51] viscosity probes, 52 pH probes, 53,54 luminescent solar concentrators (LSCs), 55 emitters for organic light-emitting diodes (OLEDs) [56][57][58][59] and robust heterocycles for dye-sensitised solar cells (DSSCs). [60][61][62] Besides interesting linear optical properties, imidazole push-pull molecules have also been investigated for their nonlinear optical (NLO) activity.…”

Section: Introductionmentioning

confidence: 99%