Design, synthesis and in vitro antitumour activity of new heteroaryl ethylenes

Fortuna, Cosimo G.; Barresi, Vincenza; Bonaccorso, Carmela; Consiglio, Giuseppe; Failla, Salvatore; Salinaro, Angela Trovato; Musumarra, Giuseppe

doi:10.1016/j.ejmech.2011.10.060

Cited by 53 publications

(65 citation statements)

References 35 publications

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“…[46,47] Measurements were performed in various organic solvents of spectroscopic grade from Sigma-Aldrich and used without further purification:c hloroform (CHCl 3 ), dichloromethane (DCM), dichloroethane (DCE), acetone (Ac), acetonitrile (MeCN), 2-propanol (2-PrOH), ethanol (EtOH), methanol (MeOH), water (W). [46,47] Measurements were performed in various organic solvents of spectroscopic grade from Sigma-Aldrich and used without further purification:c hloroform (CHCl 3 ), dichloromethane (DCM), dichloroethane (DCE), acetone (Ac), acetonitrile (MeCN), 2-propanol (2-PrOH), ethanol (EtOH), methanol (MeOH), water (W).…”

Section: Methodsmentioning

confidence: 99%

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

et al. 2015

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We report a joint experimental and theoretical investigation of a quadrupolar D-π-A(+) -π-D system, the electron donors being diphenylamino groups and the electron acceptor being a methylpyridinium, in comparison with the dipolar D-π-A(+) system. The emission spectra of the two compounds overlap in all the investigated solvents. This finding could be rationalized by TD-DFT calculations: the LUMO-HOMO molecular orbitals involved in the emission transition are localized on the same branch of the quadrupolar structure that becomes the fluorescent portion, corresponding to that of the single-arm compound. Excited-state symmetry breaking has been rarely observed for quadrupolar systems showing negative solvatochromism and is here surprisingly revealed, even in low polarity solvents. Femtosecond transient absorption measurements revealed that an efficient photoinduced intramolecular charge transfer takes place in the quadrupolar chromophore, more efficient than in its dipolar analogue. This result is promising in view of the application of these compounds as novel two-photon absorbing materials.

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Section: Methodsmentioning

confidence: 99%

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

et al. 2015

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“…29,30 The zwitterionic and cationic surfactants, p-dodecyloxybenzyldimethyl N-oxide ( pDoAO) and bis-[2-(N,N-dimethyl-N-p-dodecyloxybenzylammonium bromide)-ethyl]-ether (Gemini) (Chart 2), were used at a concentration of 0.067 M in deionized water to form homogeneous viscoelastic hydrogels for the immobilization of the substrates, by means of the experimental method that has been previously illustrated. 29,30 The zwitterionic and cationic surfactants, p-dodecyloxybenzyldimethyl N-oxide ( pDoAO) and bis-[2-(N,N-dimethyl-N-p-dodecyloxybenzylammonium bromide)-ethyl]-ether (Gemini) (Chart 2), were used at a concentration of 0.067 M in deionized water to form homogeneous viscoelastic hydrogels for the immobilization of the substrates, by means of the experimental method that has been previously illustrated.…”

Section: Methodsmentioning

confidence: 99%

Inclusion of push–pull N-methylpyridinium salts within surfactant hydrogels: is their excited state intramolecular charge transfer mediated by twisting?

Cesaretti

Carlotti

Germani

et al. 2015

Phys. Chem. Chem. Phys.

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In order to get a deep insight into the environment-dependent photophysics of push-pull pyridinium derivatives, two N-methylpyridinium salts were dissolved within surfactant hydrogels. Surfactant viscoelastic solutions can potentially block or at least limit the torsion of these fluorescent dyes, uncovering the nature of the excited states involved in their deactivation. The excited state dynamics of the two molecules in hydrogels was investigated by means of femtosecond transient absorption spectroscopy, revealing the distribution of the dyes between the hydrophobic domains and the water pools making up the microscopic structure of the surfactant hydrogels. The comparison between the spectral shapes of those transients experiencing an aqueous surrounding and those embedded in the hydrophobic domains allowed the fully relaxed excited state to be assigned to a twisted intramolecular charge transfer (TICT) state. The latter cannot be formed in the rigid hydrogel domains where the excited state charge separation is thus prevented and the stationary fluorescence comes from a scarcely polar locally excited (LE) state.

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“…19,20,[37][38][39][40][41] The experimental set-up for femtosecond fluorescence up-conversion measurements was widely described elsewhere. 19,20,[37][38][39][40][41] The experimental set-up for femtosecond fluorescence up-conversion measurements was widely described elsewhere.…”

Section: Photophysical Measurementsmentioning

confidence: 99%

An ultrafast spectroscopic and quantum mechanical investigation of multiple emissions in push–pull pyridinium derivatives bearing different electron donors

Carlotti

Benassi

Cesaretti

et al. 2015

Phys. Chem. Chem. Phys.

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A joint experimental and theoretical approach, involving state-of-the-art femtosecond fluorescence up-conversion measurements and quantum mechanical computations including vibronic effects, was employed to get a deep insight into the excited state dynamics of two cationic dipolar chromophores (Donor-π-Acceptor(+)) where the electron deficient portion is a N-methyl pyridinium and the electron donor a trimethoxyphenyl or a pyrene, respectively. The ultrafast spectroscopic investigation, and the time resolved area normalised emission spectra in particular, revealed a peculiar multiple emissive behaviour and allowed the distinct emitting states to be remarkably distinguished from solvation dynamics, occurring in water in a similar timescale. The two and three emissions experimentally detected for the trimethoxyphenyl and pyrene derivatives, respectively, were associated with specific local emissive minima in the potential energy surface of S1 on the ground of quantum-mechanical calculations. A low polar and planar Locally Excited (LE) state together with a highly polar and Twisted Intramolecular Charge Transfer (TICT) state is identified to be responsible for the dual emission of the trimethoxyphenyl compound. Interestingly, the more complex photobehaviour of the pyrenyl derivative was explained considering the contribution to the fluorescence coming not only from the LE and TICT states but also from a nearly Planar Intramolecular Charge Transfer (PICT) state, with both the TICT and the PICT generated from LE by progressive torsion around the quasi-single bond between the methylpyridinium and the ethene bridge. These findings point to an interconversion between rotamers for the pyrene compound taking place in its excited state against the Non-equilibrated Excited Rotamers (NEER) principle.

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Design, synthesis and in vitro antitumour activity of new heteroaryl ethylenes

Cited by 53 publications

References 35 publications

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

Efficient Excited‐State Symmetry Breaking in a Cationic Quadrupolar System Bearing Diphenylamino Donors

Inclusion of push–pull N-methylpyridinium salts within surfactant hydrogels: is their excited state intramolecular charge transfer mediated by twisting?

An ultrafast spectroscopic and quantum mechanical investigation of multiple emissions in push–pull pyridinium derivatives bearing different electron donors

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