Viscosity and medium effects on the fluorescence and photochemical behaviour of some aryl chalcones

doi:10.1016/0009-2614(88)87454-2

Chemical Physics Letters

Volume 146, Issues 3–4, 6 May 1988, Pages 331-336

https://doi.org/10.1016/0009-2614(88)87454-2 Get rights and content

Abstract

The emission, excitation and absorption spectra toghether with the fluorescence and photochemical quantum yields of some chalcone derivatives have been studied in organic solvents and micellar and microemulsion media. Both 4-[2-(2-pyridyl)ethenyl] (I) and 4-[2-(4-pyridyl)ethenyl (II) chalcones show large positive solvatochromic effects. The fluorescence quantum yields increase substantially as the medium viscosity increases with a subsequent decrease in the photochemical quatum yield. Compounds I and II undergo excited-state molecular aggregation in concentrated solutions giving excimer-like emission that coincides with emission from crystalline samples. The enthalpies of photoassociation have been estimated. The chalcone derivative I acts as an efficient quencher of the fluorescence of the laser dye 1,4-bis (β-pyridyl-2-vinyl)benzene via a long-range mechanism. The excited-state lifetimes of both I and II are short and at 20°C their τ values are less than 800 ps.

References (26)

G.A. Delzenne
B. Stevens
Advan. Photochem.
(1971)
M. Hasegawa
Advan. Polym. Sci.
(1982)
M. Hasegawa
Chem. Rev.
(1983)
M. Hasegawa
Pure Appl. Chem.
(1986)
W.L. Dilling
Chem. Rev.
(1983)
E.M. Ebeid et al.
Laser Chem.
(1985)
E.M. Ebeid et al.
J. Chem. Soc.
(1986)
H. Telle et al.
Opt. Commun.
(1978)
K. Norland et al.
Photogr. Sci. Eng.
(1970)
J.H. Fendler
J. Phys. Chem.
(1980)
J. Kordas et al.
J. Am. Chem. Soc.
(1974)

J.V. Morris et al.

J. Phys. Chem.

(1976)

J.N. Demas et al.

J. Phys. Chem.

(1971)

E.M. Ebeid et al.

J. Chem. Soc.

(1986)

Cited by (18)

Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base
2024, Heliyon
A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of p-phenylenediamine with 2-hydroxy-1-naphthaldehyde and 4-nitrobenzaldehyde and characterized with spectroscopic analysis. UV-VIS and NMR. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. Density functional theory (DFT) calculations were performed to study the mechanism of reaction for the synthesis of 4NMN, and the results were consistent with the experimental findings. 4NMN exhibited moderate antibacterial and antifungal activities and demonstrated higher inhibition potential against different resistant strains compared to the reference drug gentamycin. The absorption and fluorescence spectra of 4NMN were measured in different solvents, and the effect of relative polarity and acidity on the medium was observed. An inner filter effect was observed at high concentrations, and the compound showed considerable fluorescence enhancement with increasing medium viscosity and fluorescence quenching by the addition of traces of Cr¹⁺ and Cu²⁺. Additionally, molecular docking studies were conducted to investigate the efficiency of antibacterial and antifungal targets.
Colorimetric detection of Cu(II) ion with a 1,3-bis-azachalcone derivative
2015, Sensors and Actuators, B: Chemical
Citation Excerpt :
The naturally occurring chalcones, the biosynthetic precursor to many flavonoids, are known to perform various biological activities [9–11] along with their aza-derivatives which contain annular nitrogen atoms in phenyl ring. Such derivatives show large positive solvatochromic effect [12] due to existence of donor–acceptor assembly favouring an intra molecular charge transfer [13] and therefore of have drawn recent interest in their applications as materials in optical limiting [14], non-linear optical (NLO) [15], electrochemical sensing [16], Langmuir–Blodgett films [17] and photo-reactivity [18] assessment; apart from their utility as fluorogenic chemosensor for determination and quantification of water content in organic solvents [19] and saccharides estimation [20]. The azachalcone derivatives are also envisaged to form complexes with various metal ions due to existence of suitable coordinating sites in form of pyridyl and enones segments in their architecture although such complexes are not extensively known.
A symmetrical bis-azachalcones derivative L exhibited photophysical spectral perturbation along with simultaneous colour change from colourless to greenish yellow particularly in the presence of Cu(II) ion. The stereo-electronic contribution of complexation, in turn, a different coordination module enabled it to be a probe for the metal ion's selective colorimetric detection among all metal ions investigated. Its reversible signalling pattern as well as colour transition of its Cu(II) complexation selectively with l-proline through a displacement approach is also promising as chemosensing probe for the amino acid.
Spectral properties and micellization of 1-(2,5-Dimethyl-thiophen-3-yl)-3- (2,4,5-trimethoxy-phenyl)-propenone (DTTP) in different media
2013, Journal of Luminescence
Citation Excerpt :
Solutes showing a charge transfer band often serve as reporter molecules of the surrounding environment. Donor–acceptor chalcone dyes form a class of compounds which are characterized by the above properties [2–6]. They have been applied in the food industry and photoreactive polymers [7].
The parameters of the electronic absorption and emission spectra of 1-(2,5-dimethyl thiophen-3-yl)-3-(2,4,5-trimethoxy-phenyl)-propenone (DTTP) were measured in different solvents; DTTP exhibits a red shift in its emission spectrum as solvent polarity increases, indicating a large change in dipole moment upon excitation due to intramolecular charge transfer in excited DTTP^⁎. Excited state intermolecular hydrogen bonding affects the energy of the emission spectrum, fluorescence quantum yield and fluorescence lifetime of DTTP. The dye undergoes micellization in different micelles and may be used as a probe to determine the critical micelle concentration (CMC) of SDS, CTAB and TX-100.
Photophysical parameters and laser activity of 3(4-dimethylamino-phenyl)-1- (2, 5-dimethyl-thiophen-3-yl)-propenone (DDTP): A new potential laser dye
2013, Optics and Laser Technology
Citation Excerpt :
Chalcone derivatives have been reported earlier as important probes of medium viscosity [1].
The photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra and fluorescence quantum yield of DDTP were measured in different solvents. DDTP dye exhibits red shift in both absorption and emission spectra as solvent polarity increases, indicating that the dipole moment of DDTP dye is higher in excited state than that in the ground state. The density functional calculation were used to obtain the ground state and excited state dipole moments for it has proven to be suitable for calculating electronic excitation energy. A crystalline solid of DDTP gives excimer like emission at 575 nm. The absorption and emission spectra of DDTP have been investigated in organized media of aqueous micellar solution. The critical micelle concentration (CMC) of sodium dodecyl sulphate (SDS), cetyltrimethyl ammonium bromide (CTAB) and triton X-100 (TX-100) are determined using DDTP dye. Dye solution ca 1×10⁻³ mol dm⁻³ in dimethyl sulfoxide (DMSO) gives laser emission in the range 490–560 nm with emission maximum at 520 nm upon pumping by nitrogen laser (337.1). The gain coefficient (α) and emission cross section σ_e at maximum laser emission are also determined.
Spectroscopic studies and laser activity of 3-(4-dimethylamino-phenyl)-1- (2,5-dimethyl-furan-3-yl)-propenone (DDFP): A new green laser dye
2013, Journal of Luminescence
Citation Excerpt :
Chalcone derivatives have been reported earlier as important probes of medium viscosity [1].
Photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra, and fluorescence quantum yield of DDFP were measured in different solvents. DDFP dye exhibits an essentially larger redshift of the emission spectra than the absorption one as solvent polarity increases. This fact indicates that the dipole moment of the DDFP dye is higher in singlet excited state than that in the ground one. A crystalline solid of DDFP gives excimer like emission at 575 nm. The absorption and emission spectra of DDFP have been investigated in organized media of aqueous micellar solutions. The critical micelle concentration (CMC) of sodium dodecyl sulfate (SDS) and cetyltrimethyl ammonium bromide (CTAB) are determined using DDFP dye. The photoreactivity and the net photochemical quantum yield (φ_c) of DDFP dye was determined in different solvents. The dye is relatively photostable in DMSO but undergoes photodecomposition in chloromethane solvents. Dye solution circa 1×10⁻⁴ mol dm⁻³ in dimethyl sulfoxide (DMSO) gives laser emission in the range 490–560 nm with emission maximum at 515 nm upon pumping by nitrogen laser (337.1). The gain coefficient (α) and emission cross section σ_e at maximum laser emission are also determined.
Spectral behavior and laser activity of 3-(4′-dimethylaminophenyl)-1-(1H-pyrrol-2-yl) prop-2-en-1-one (DMAPrP). A new laser dye
2010, Optics and Laser Technology
The photophysical properties of DMAPrP have been investigated in different solvents. DMAPrP dye exhibits a large change in dipole-moment upon excitation due to an intramolecular charge transfer interaction. A crystalline solid of DMAPrP give an excimer like emission at 546 nm. The ground and excited state protonation constants of DMAPrP are calculated. DMAPrP acts as good laser dye upon pumping with nitrogen laser in some organic solvents. The laser parameters such as the tuning range, gain coefficient (α), emission cross section (σ_e) and half-life energy (E_1/2) are also calculated. The photoreactivity and net photochemical quantum yield of DMAPrP in chloromethane solvents are also studied.

View all citing articles on Scopus

View full text

Viscosity and medium effects on the fluorescence and photochemical behaviour of some aryl chalcones

Abstract

Advan. Photochem.

Advan. Polym. Sci.

Chem. Rev.

Pure Appl. Chem.

Chem. Rev.

Laser Chem.

J. Chem. Soc.

Opt. Commun.

Photogr. Sci. Eng.

J. Phys. Chem.

J. Am. Chem. Soc.

J. Phys. Chem.

J. Phys. Chem.

J. Chem. Soc.