Synthesis, spectral properties and photobehaviour of push–pull distyrylbenzene nitro-derivatives

Kikaš, Ilijana; Carlotti, Benedetta; Škorić, Irena; Šindler‐Kulyk, Marija; Mazzucato, U.; Spalletti, Anna

doi:10.1016/j.jphotochem.2012.06.009

Cited by 27 publications

(14 citation statements)

References 22 publications

(39 reference statements)

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“…[1][2][3][4][5] The effect of substituents on the photobehaviour of stilbene and related molecules has been widely investigated in the last two decades, 6,7 particularly the effect of D/A substituents on the excited state deactivation (for some significant contributions see ref. [1][2][3][4][5] The effect of substituents on the photobehaviour of stilbene and related molecules has been widely investigated in the last two decades, 6,7 particularly the effect of D/A substituents on the excited state deactivation (for some significant contributions see ref.…”

Section: Introductionmentioning

confidence: 99%

Unusual high fluorescence of two nitro-distyrylbenzene-like compounds induced by CT processes affecting the fluorescence/intersystem-crossing competition

Carlotti

Elisei

Mazzucato

et al. 2015

Phys. Chem. Chem. Phys.

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Two nitro-substituted 1,4-distyrylbenzene-like compounds have been investigated using stationary and time-resolved (ns/fs) spectrometric techniques as a function of solvent polarity. In the two compounds the central benzene ring is substituted with a p-nitrostyryl group at one side while, at the other side, compound 1 (asymmetric) bears a pyrid-4-ylethenyl group and compound 2 (symmetric) another p-nitrostyryl group. The solvent dependent intramolecular charge transfer (ICT) in the singlet manifold was found to strongly affect the competition among fluorescence, intersystem crossing and trans-cis photoisomerization. The presence of nitro-groups in the 1,4-distyrylbenzene skeleton causes the usual strong decrease of fluorescence in favour of intersystem crossing to a reactive triplet state. However, the favoured formation of the ICT state in polar solvents induces an unexpected important increase of the fluorescence quantum yield (three/two order of magnitude for the nitro and dinitro derivatives, respectively). The ultrafast spectral transients helped to understand the solvent effects measured by stationary techniques and gave information on the dynamics of the locally excited singlet state ((1)LE*) and the (1)ICT* state, fast produced in polar solvents. Evidence of dual fluorescence in a limited range of solvent polarity, particularly for compound 1, is also reported. The role of an upper triplet state in a non-polar solvent is discussed also based on quantum-mechanical calculations (TD-DFT method) and temperature effects on the photophysical parameters.

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Section: Introductionmentioning

confidence: 99%

Unusual high fluorescence of two nitro-distyrylbenzene-like compounds induced by CT processes affecting the fluorescence/intersystem-crossing competition

Carlotti

Elisei

Mazzucato

et al. 2015

Phys. Chem. Chem. Phys.

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“…The absorption and emission spectra of compounds having furan and thiophene are redshifted with respect to the pyridine derivative on account of their highly conjugated structures. The poorly aromatic nature of furan and thiophene accounts for the appearance of absorption and emission band at higher energy . Replacement of carbon atoms by heteroatoms in the skeleton depends more on the position of the inserted heteroatoms than on their nature.…”

Section: Resultsmentioning

confidence: 99%

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Mohan

Satyanarayan

Trivedi

2019

J of Physical Organic Chem

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Hydrazides are known to exhibit keto‐enol tautomerism upon photoexcitation. Theoretical aspects uncovering excited state intramolecular proton transfer (ESIPT) of N‐acylsubstituted hydrazides with bithiophene core have been investigated. Geometrical aspects of the system are expected to undergo double proton translocation at its excited state. However, potential energy surface study for all the molecules reveals an impossible concurrent double proton translocation and to a greater extent dubious step‐wise double proton translocation in the system. Potential energy scans reveal molecules possessing a lower forward barrier at its excited state in comparison with their ground state suggestive of possible excited state single proton transfer. Geometrical attributes and spectral analysis suggest the strengthening of intramolecular hydrogen bond (N―H▪▪▪O) at its excited state, favoring single proton translocation. Theoretical estimation of electronic energy transition for all the conformers yields good correlation with the experimental figures with an energy overestimation <0.17 eV.

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“…[24][25][26][27][28] A phosphonium salt with a methoxy group in the para position of the phenyl ring was used to give compounds 6a and 6d. [24][25][26][27][28] A phosphonium salt with a methoxy group in the para position of the phenyl ring was used to give compounds 6a and 6d.…”

Section: Full Papermentioning

confidence: 99%

“…The required p-and ophenyl-substituted 5-arylethenyloxazoles were prepared from the corresponding α, -unsaturated aldehydes and the TosMIC reagent (tosylmethyl isocyanide) by the Van Leusen reaction. [24][25][26][27][28] A phosphonium salt with a methoxy group in the para position of the phenyl ring was used to give compounds 6a and 6d. Synthesis of 4-styryloxazoles 5a-5c, 6a-6c, 7a, and 7b and 4-(2-methylstyryl)oxazoles 5d, 6d-6f, 7c, and 7d.…”

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Synthesis of Naphthoxazoles by Photocyclization of 4‐/5‐(Phenylethenyl)oxazoles

et al. 2018

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Promising test results on the biological activity of our previously described naphtho[1,2‐d]oxazoles and heterobenz[1,2‐d]oxazoles, obtained by the photochemical cyclization of 5‐phenylethenyl‐ and 5‐heteroarylethenyloxazoles, prompted us to continue with the photochemical synthesis of substituted naphtho[1,2‐d]oxazoles, and to extend the photochemical cyclization to the synthesis of naphtho/heterobenz[2,1‐d]oxazoles from 4‐(aryl/heteroarylethenyl)oxazoles. The required p‐ and o‐phenyl‐substituted 5‐arylethenyloxazoles were prepared from the corresponding α,β‐unsaturated aldehydes and the TosMIC reagent (tosylmethyl isocyanide) by the Van Leusen reaction. The substituted 4‐(aryl/heteroarylethenyl)oxazoles were prepared by the Wittig reaction starting from various phosphonium salts and 2‐H/methyl‐4‐oxazolecarbaldehydes.

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Synthesis, spectral properties and photobehaviour of push–pull distyrylbenzene nitro-derivatives

Cited by 27 publications

References 22 publications

Unusual high fluorescence of two nitro-distyrylbenzene-like compounds induced by CT processes affecting the fluorescence/intersystem-crossing competition

Unusual high fluorescence of two nitro-distyrylbenzene-like compounds induced by CT processes affecting the fluorescence/intersystem-crossing competition

Exploring the possibilities of double proton transfer in hydrazides: A theoretical approach

Synthesis of Naphthoxazoles by Photocyclization of 4‐/5‐(Phenylethenyl)oxazoles

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