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Dokuz Eylul University | DEÜ · Department of Chemistry
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We describe the characterization of a new optical CO(2) sensor based on the change in the fluorescence signal intensity of 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (HPTS) in green chemistry reagents--room-temperature ionic liquids (RTILs). As far as we are aware, this is the first time RTILs, 1-methyl-3-butylimidazolium tetrafluorobora...
3,6-diaryl-2,5-dihydro-1,4-diketopyrrolo[3,4-c]pyrrole-1,4-dione (DPPD) derivatives are used commercially as red pigments, because of their color strength, brightness, and very low solubility in most common solvents. These products, although highly colored, appear to be of limited value as dyes, since they show a tendency to form an aggregate when...
A highly sensitive fluorescent enzyme array for quantitative acetylcholine detection is developed. The enzyme array has been constructed by spotting of pH sensitive fluorophore 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacycloopentadecyl)benzylidene]oxazol-5-one and acetylcholinesterase doped in tetraethoxysilane/chitosan matrix via a microarrayer. The...
The asymmetric unit of the title compound, C(30)H(36)N(2)O(2), contains one half-mol-ecule, the other half being generated by a crystallographic inversion centre. The crystal structure is devoid of any classical hydrogen bonds however, non-classical C-H⋯O inter-actions link the mol-ecules into chains propagating in [001] and a C-H⋯π inter-action le...
In the title compound, C(24)H(15)NO(2), the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intra-molecular C-H⋯N hydrogen bonds link the oxazole N atom to the naphthalene ring systems. I...
Seven fluorescent thiophene-based oxazol-5-one derivatives were prepared via Erlenmeyer reaction of 2-thiophenecarboxaldehyde and 3-thiophenecarboxaldehyde with different aryl glycine intermediates. Their absorption and emission properties were investigated in solution environment and in the solid film matrix of polyvinylchloride. Moreover, the flu...
The aim of this study is to synthesize oxazol-5-one derivatives, which have multi-functional properties. Nomenclatures of newly synthesized molecules are 4-(4-N,N-diethylaminophenylmethylene)-2-(3-thienyl)oxazol-5-one (4a) and 4-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)phenylmethylene)-2-(3-thienyl)oxazol-5-one (4b). These two novel derivatives...
In this study, copolymers were synthesized using methyl methacrylate (MMA) and 2-allyloxymethyl-1-methylimidazole (AOMMI) monomers at various ratios. For this purpose, hydroxyl end-functionalized imidazole was initially prepared with 1-methylimidazole and then it was used to prepare allyl-derived imidazole monomers. Finally, the synthesis of copoly...
New fluorescent thiophenyl group containing oxazol-5-one fluorophores of 3a (4-(3-thiophenylmethylene)-2-phenyloxazol-5-one), 3b (4-(3-thiophenylmethylene)-2-(4-tolyl)oxazol-5-one) and 3c (4-(3-thiophenylmethylene)-2-(4-nitrophenyl)oxazol-5-one) were synthesized and characterized. The newly synthesized oxazol-5-ones absorption and fluorescence char...
In this study, two oxazol-5-one derivatives, C20H20N2O2 (1) and C21H22N2O2 (2), were synthesized by getting condensed p-N,N-diethylaminobenzaldehyde with two presented hippuric acid derivatives and in further studies they were analysed spectrochemically. Molecular and crystal structures of the compounds were determined by single-crystal X-ray diffr...
In this study, two oxazol-5-one derivatives, C20H20N2O2 (1) and C21H22N2O2 (2), were synthesized by getting condensed
p-N,N-diethylaminobenzaldehyde with two presented hippuric acid derivatives and in further studies they were analysed
spectrochemically. Molecular and crystal structures of the compounds were determined by single-crystal X-ray
diffr...
A set of new oxazol-5-one fluorophores incorporating ethylene glycol chains terminated with an aldehyde unit has been synthesized and characterized structurally. Two pairs of compounds can be distinguished according to the substitution on the oxazol-5-one moiety: one pair bears a tolyl unit and the other a nitrophenyl unit. The difference within th...
Coumarin-oxazol-5-one (COX), 3a-d, were synthesized with 7-methoxy-2-oxo-2H-chromene-4-carbaldehyde and benzoylglycine derivatives. The characterizations of the COX derivatives by ¹H NMR, FT-IR and elemental analysis were achieved. To obtain the photophysical data of the synthesized COX derivatives were used spectrophotometric and spectrofluorimetr...
New anthracene oxazol-5-one dyes featuring an extended π-conjugated electron system have been successfully prepared by Erlenmeyer synthesis, structurally characterized and their spectroscopic properties were investigated by UV–vis absorption spectroscopy and fluorescence spectroscopy. The oxazol-5-ones were attached to the 9-position of the anthrac...
4-(4′-acetyloxy-3′-methoxybenzylidene)-5-oxazolone fluorescent molecules bearing four different aryl groups attached to the 2-position of 5-oxazolone ring have been investigated by spectrophotometric and potentiometric techniques in solution media. The acidity constants (pKa) of the fluorescent molecules were precisely determined in acetone, aceton...
2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione derivatives (DPP) are chemically stable, fluorescent molecules, known as High Performance Pigments. Preparation of the soluble derivatives of DPPs provides great advantage in designing the optic sensor for new and existing applications and overcoming aggregation problems in solid matrices. For this purpose...
The solvatochromic and spectral properties of oxazolone derivatives in various solvents were reported. Fluorescence spectra clearly showed positive and negative solvatochromism depending on substituents. The solvatochromic plots and quantum chemical computations at DFT-B3LYP/6-31 + G(d,p) level were used to assess dipole moment changes between the...
A new optical dissolved carbon dioxide (dCO2) sensor based on the spectrofluorimetric signal changes of the fluorescent carbazole derivative in room temperature ionic liquid was proposed. Response of the offered sensor composition to gaseous and dissolved carbon dioxide was tested in ethyl-cellulose- and imidazolium-based ionic liquid moieties. The...
Molecular and crystal structure of 4-[(p-N,N-dimethylamino)benzylidene]-2-phenyloxazol-5-one, C(18)H(16)N(2)O(2), have been determined by single crystal X-ray diffraction study. The title compound is monoclinic, with a = 12.1704(23) , b = 3.9810(5) , c = 30.9603(56) , beta = 101.176(15)A degrees, Z = 4, D (x) = 1.32 g/cm(3), mu(Mo K alpha) = 0.087...
The asymmetric unit of the title compound, C(18)H(11)NO(2)S, contains two crystallographically independent mol-ecules. In one mol-ecule, the oxazole and thio-phene rings are oriented at dihedral angles of 17.40 (9) and 18.18 (7)° with respect to the naphthalene ring system, while the oxazole and thio-phene rings are oriented to each other at a dihe...
Optical glucose oxidase (GOx) arrays based on pH sensitive fluorescent dye (2-(4-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone) (CPO) has been constructed. The arrays were prepared by spotting of CPO and GOx together with tetraethoxysilane (TEOS)/Chitosan (CHIT) mixture via a microarrayer. After optimization studies,...
A novel oxazole-5-one derivative 2-o-tolyl-4-(3-N,N-dimethylaminophenylmethylene)-oxazol-5-one (TDPO) C(19)H(18)N(2)O(2) is synthesized and characterized and the crystal structure is determined by X-ray crystallography. TDPO is monoclinic in the P2(1)/c space group. The molecule adopts the Z configuration. To enlighten the flexibility of TDPO, the...
A novel oxazole-5-one derivative 2-o-tolyl-4-(3-N,N-dimethylaminophenylmethylene)-oxazol-5-one (TDPO) C19H18N2O2 is synthesized and characterized and the crystal structure is determined by X-ray crystallography. TDPO is monoclinic in
the P21/c space group. The molecule adopts the Z configuration. To enlighten the flexibility of TDPO, the selected t...
Compounds (I) are prepared by an Erlenmeyer reaction and show promising photochemical properties.
The interactions between bovine serum albumin (BSA) and two substituted hydroxychromone derivatives of coumarin, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-on (C3) and 1,3-dihydroxy-7,8,9,10-tetrahy-dro-6H-benzo[c]chromen-6-on (C1.3), were investigated by fluorescence quenching spectra and UV-vis absorption spectra. It was proved that the f...
Here we present a new sol-gel based fluorescent glucose biosensor. The sensor is based on the pH sensitive fluorescent dye entrapped in a tetraethoxysilane (TEOS) based sol-gel together with glucose oxidase. Micro-analytic system which can measure the pH induced chance in the fluorescence intensity due to the enzymatic reaction in spotted layer on...
An azlactone derivative, 4-[(p-N,N-dimethylamino)benzylidene]-2-(3,5-dinitrophenyl)oxazol-5-one (DNPO), C18H14N4O6, has been synthesized, and its crystal structure has been investigated by single crystal X-ray analysis and ab initio method. DNPO is monoclinic, with a=9.3628(4), b=13.5148(9), c=13.7701(6), =92.921(4), Z=4, Dx=1.46g/cm3, (MoK)=0.112m...
Reversible biosensors based on 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-I), 2-(4-nitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-II) and 2-(4-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-III) derivatives immobilize...
Pyrrolobenzosulfonamide, indolobenzosulfonamide and carbazolobenzosulfonamide derivatives with different acceptor groups were synthesized and their photophysical properties were compared. The electron donor linking sites are found to influence the emission characteristics of these compounds while acceptor linking sites have no noticeable effects on...
Room temperature ionic liquids doped with tris(2,2′-bipyridyl)ruthenium(II)chloride together with chemically and biochemically
inert perfluoro chemicals (PFCs) have been used for the first time for optical O2 sensing purposes.

The response to oxygen of the Ru complex in 1-methyl-3-butylimidazolium tetrafluoroborate (RTIL-I) and 1-methyl-3-butylimi...
Fully reversible biosensors for glucose monitoring based on solid polyvinylchloride (PVC) films where the enzyme glucose oxidase (GOx) was incorporated together with 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadec yl)benzylidene]-5-oxazolone (CPO-1), 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10- tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone...
The photophysical and photochemical properties of azlactone derivative 4-(2-furylmethylene)-2-phenyl-5-oxazolone (PFO) were examined in solvents of tetrahydrofuran (THF), acetonitrile (ACN) and dichloromethane (DCM) and in solid matrix of polyvinyl chloride (PVC).The PFO dye embedded in plasticized PVC matrix has been used in monitoring Fe3+. The P...
Novel 5-oxazolone derivatives containing an N-phenyl-aza-15-crown-5 moiety were synthesized for the first time. The structures of the new derivatives were confirmed by 1H NMR, 13C NMR and FT-IR. In addition, evaluation of the visible absorption and emission properties of the structures were carried out in eight different solvents. The products show...
A new 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO) derivative was utilized to develop an optical acetylcholinesterase (AChE) biosensor in which the azlactone derivative was embedded in plasticized polyvinylchloride (PVC) matrix. The sensor system was calibrated for the detection of acetylcholine (ACh) and do...
Molecules of the title compound, C(24)H(19)NO(6)S, adopt the Z configuration and have a distorted tetrahedral geometry around the S atom. The oxazolone, 2-phenyl and methoxyphenyl rings are approximately coplanar. The C atom between the methoxyphenyl and oxazolone rings displays a distorted trigonal bonding geometry. Pairs of molecules are linked i...
A new optical CO2 sensor based on the spectrophotometric signal changes of the bromothymol blue/tetraoctylammonium (BTB−/TOA+) ion pair in room temperature ionic liquids (RTILs) has been proposed. Ionic liquids, also known as green chemistry reagents, have been used for the first time as a matrix material in the optical CO2 sensor design. In the fi...
An emission based simple and fast method has been proposed for the determination of gaseous and dissolved CO2. Perfluorochemicals (PFCs), also known as medical gas carriers have been used for the first time together with newly synthesized fluorophore; 4-[(p-N,N-dimethylamino)benzylidene]-2-phenyloxazole-5-one (DPO), in ethyl cellulose matrix. In th...
The proton sensitive azlactone derivative; 4-[(p-N,N-dimethylamino)benzylidene]-2-phenyloxazole-5-one (DPO) exhibits high quantum yield, excellent photostability, and high molar absorptivity in a sol–gel matrix. In this work, two different DPO containing constructions were tested and evaluated as glucose sensors. In the first, both glucose oxidase...
Thermal stabilities, solubilities redox potentials and photophysical parameters of 10 synthesized N-alkyl(aryl) derivatives of naphthalene diimides were studied for selecting the best derivatives at concentrated sun light experiments. N-aryl substitutions created better thermal stabilities than the N-alkyl substitution in naphthalene diimides. LUMO...
4-Arylidene-2-aryl-5-oxazolone (azlactone) structures have wide range of applications arising from their promising photophysical and photochemical activities. Some of this class of dyes exhibit pH-dependent absorption and emission based response. For this reason, precise determination of the acidity constants (pKa) of the azlactone derivatives is n...
A systematic quantitative study of the solubility of various naphthalene diimides in apolar and polar solvents with different lipophilicity has been done by means of UV–vis spectroscopy.It has been found that the most soluble naphthalene diimide derivative is N,N′-bis(dehydroabietyl)-1,4,5,8-naphthalene diimide.The conclusion that the introduction...
In this study, the photophysical characteristics, like molar extinction coefficients, Stoke's shifts, quantum yields, radiative and fluorescence lifetimes, fluorescence rate constants, radiationless deactivation rate constants, and singlet energies of the fluorescent mesomorphic diketopyrrolopyrrole derivatives, (DPPDs), 3,6-bis(4-octyloxyphenyl)-2...
The spectral-luminescent properties and electrochemistry of the N,N′-bis-n-butyl derivative of naphthalene diimide were studied. The main photophysical parameters (quantum yield, rate constants of fluorescence and of non-radiative deactivation and fluorescence lifetime) were determined. The LUMO value (-3.51 eV) was determined by cyclic voltammetry...
The photophysical and photochemical properties of an azlactone derivative, 4-(p-N,N-dimethylaminophenylmethylene)-2-phenyl-5-oxazolone, (DPO) in a sol-gel matrix have been examined. The fluorescence quantum yield, radiative lifetime, fluorescence lifetime, fluorescence rate constant and singlet energy values of the DPO dye were determined in a modi...
Azlactone molecules can be protonated in acidic media, and the process of protonation is irreversible due to ring opening in solutions. A new fully reversible pH sensor has been developed 4-(p-N,N-dimethylamino phenyl methylene)-2-phenyl-5-oxazolone (DPO), an azlactone derivative, embedded in a plasticized PVC polymer film. The sensor membrane is c...
Seven derivatives of naphthalene diimides, synthesized, have shown similar photophysical properties. Low fluorescence quantum yields (0.002–0.006) and short fluorescence lifetimes (5–18 ps) have suggested rapid intersystem crossing processes from excited singlet state. Quenching of fluorescence emissions of aromatic donor molecules, i.e. naphthalen...
The fluorescent properties of several natural benzofuran derivatives, egonols, isolated from Styrax officinales, were determined. The studied egonol derivatives were found to be effective UV organic luminophores, with quantum yields of near to unity, φf = 0.92. The fluorescence quenching experiments with electron donor molecules of aniline, N,N-dim...
The fluorescent properties of several natural benzofuran derivatives, egonols, isolated from Styrax officinalis, were determined. The studied egonol derivatives were found to be effective UV organic luminophores, with quantum yields of near to unity, phi(f) = 0.92. The fluorescence quenching experiments with electron donor molecules of aniline, N,N...
Experimental and theoretical evaluations have proven that very low fluorescence quantum yields of azlactones in solution are not caused by an efficient inter system crossing from S1*(ππ) to T*(nπ) states, but rather from solvation and steric effects, that result in non-planarity of the molecular system. High fluorescence quantum yields in the solid...
Absorption and fluorescence wavelengths for a series of a lactones have been measured from acetonitrile solutions that had no pre-light exposure. Fluorescence quantum yields, Qp are found to be in general less than 0.01, excluding the the derivatives with naphthyl and p-dimethylaminophenyl substituents. Previously reported QF values did not not fit...
Department of Chemistry İzmir, Turkey
Department of Materials Engineering
Department of Biochemistry and Molecular Biology
Department of Pharmaceutical Science and Research
Institute of Microsystem and Precision Manufacturing Engineering
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