Three azine oligomeric esters were synthesized, characterized by IR, UV, 1H, 13C{1H} and GPC technique, and applied to chemosensor application. The sensitivity response of the oligomers towards the metal ion was evaluated for a metal ion series. The results have shown selective and sensitive “turn off” fluorescence response towards Fe3+ ion in DMF/H2O (1:1, pH: 7.4, fluorophore: 5 μM) solution. The binding stoichiometry and binding constant of the fluorophores were calculated using the Stern–Volmer equation and Benesi–Hildebrand plots, respectively. The quenching of fluorophores on the addition of Fe3+ ion indicates the capability of fluorophore towards quantitative analysis of Fe3+. The dimer of oligomers was theoretically studied using DFT, B3LYP/6-311G level basic set to support and explain the quenching mechanism of LMCT, PET process and to explain the DC, AC electrical studies results. The electrical conductivity measurements of solid-state, I2 doped and undoped oligomers were carried out and the conductivity gradually increases with increase in iodine vapor contact time of oligomers. The electrical conductivity was related with band gap and charge density values of imine nitrogen obtained by Huckel calculations. The dielectric measurements at different temperatures and frequencies were made by two probe method. Among the oligomers, EBHAP has recorded a high dielectric constant at the low applied frequency of 50 Hz at 373 K due to loosely attached π bonds resulting good polarization.
MahajanPGKolekarGBPatilSR. Fluorescence-based logic gate for sensing of Ca2+ and F− ions using PVP crowned chrysene nanoparticles in aqueous medium. Luminescence2017; 32: 845–855.
2.
CuiWWangLXiangG, et al.A colorimetric and fluorescence “turn-off” chemosensor for the detection of silver ion based on a conjugated polymer containing 2,3-di(pyridin-2-yl)quinoxaline. Sens Actuators B Chem2015; 207: 281–290.
3.
GomesDMCSegundoMALimaJLFC, et al.Spectrophotometric determination of iron and boron in soil extracts using a multi-syringe flow injection system. Talanta2005; 66: 703–711.
4.
LunvongsaSOshimaMMotomizuS. Determination of total and dissolved amount of iron in water samples using catalytic spectrophotometric flow injection analysis. Talanta2006; 68: 969–973.
5.
ChangVCCotterchioMKhooE. Iron intake, body iron status, and risk of breast cancer: a systematic review and meta-analysis. BMC Cancer2019; 19: 543.
6.
Johnson-WimbleyTDGrahamDY. Diagnosis and management of iron deficiency anemia in the 21st century. TAG2011; 4(3): 177–184.
7.
GviliAGSchechterARozen-ZviB. Iron deficiency anemia in chronic kidney disease. Acta Haematol2019; 142: 44–50.
8.
MullerM. Leavitt BR, ron dysregulation in Huntington’s disease. J Neurochem2014; 130: 328–350.
9.
AytonSWangYDioufI, et al.Brain iron is associated with accelerated cognitive decline in people with Alzheimer pathology. Mol2019; 25: 2932–2941.
10.
MedeirosMSSchuhASCardosoAM, et al.Iron and oxidative stress in Parkinson’s disease: an observational study of injury biomarkers. PLoS One2016; 11: 1–12.
11.
NilssonUABassenMSavmanK, et al.A simple and rapid method for the determination of free iron in biological fluids. Free Radic Res2002; 36: 677–684.
12.
SaidARSaidKAwwadF, et al.Design, fabrication, and characterization of Hg2+ sensor based on graphite oxide and metallic nanoclusters. Sensor Actuat A-Phys2018; 271: 270–277.
13.
PepperSEBorkowskiMRichmannMK, et al.Determination of ferrous and ferric iron in aqueous biological solutions. Anal Chim Acta2010; 663: 172–177.
14.
SaleemMAbdullahRAliA, et al.Facile synthesis, cytotoxicity and bioimaging of Fe3+ selective fluorescent chemosensor. Bioorg Med Chem Lett2014; 22: 2045–2051.
15.
McquadeDTHegedusAHSwagerTM. Signal amplification of a “turn-on” sensor: Harvesting the light captured by a conjugated oligomer. J Am Chem Soc2000; 122: 12389–12390.
16.
KaraogluKSerbestKEmirikM, et al. An unsymmetrical ferrocene based azine and its Cu (II) complex: Spectroscopy, crystal structure, electrochemistry and DFT calculations. J Organomet Chem2015; 775: 80–87.
17.
LiuYWeiYBianY, et al.A 2-(benzo[d]thiazol-2-yl)phenol based on conjugated polymer: Highly selective colorimetric fluorescent chemosensor for F-depending on Si–O bond cleavage reaction. High Perform Polym2020; 32: 344–356.
18.
NaJHKimYSParkWH, et al.Metal-induced optical sensing and optical switching in poly(pyridyl phenylene). J Polym Sci Pol Chem2004; 42: 2444–2450.
19.
OmerNZhangFZhaoG, et al.Highly selective chemo-sensor for repetitive detection of Fe3+ in pure water and bio-imaging. Analyst2019; 144: 3414–3421.
20.
ShengRWangPLiuW, et al. A new colourimetric chemosensor for Hg2+ based on coumarin azine derivative. Sensor Actuat B-Chem2008; 128: 507–511.
21.
ArmaregoWLFChaiCLL. Purification of Laboratory Chemicals. Australia: Canberra ACT, 2002.
22.
ManigandanSMuthusamyANandhakumarR, et al.Recognition of Fe3+ by a new azine-based fluorescent “turn-off” chemosensor and its binding mode analysis using DFT. J Mol Struct2020; 1208: 127834.
23.
ChandrasekaranSRSharmaBK. Fuel properties associated with catalytic conversion of plastics. Plastics to Energy, United States, Champaign, IL,2019; 173–200, doi:org/10.1016/B978-0-12-813140-4.00007-8.
24.
BiliciAKayaIYıldırımM. A comparative study of 9,9-bis (4-aminophenyl) fluorene polymers prepared by catalytic and non-catalytic oxidative polymerization methods. Eur Polym J2011; 47: 1005–1017.
25.
AnandSMuthusamyAKannapiranN. Synthesis, characterization, thermal, electrical and electrochemical studies of oligonitrobenzimidazoles and their p–n diode applications. J Mater Sci Mater EL2018; 29: 13429–13441.
26.
ChowdhurySChandaTKoleyS, et al.Regioselective dehydrative intramolecular heteroannulation of β-allyl- β-hydroxy dithioesters: facile and straightforward entry to 2H -thiopyrans. Tetrahedron2014; 70: 914–918.
27.
ShuklaGVermaGKNagarajuA, et al.DMAP mediated one-pot domino thienannulation : a versatile, regioselective and green mechanochemical. RSC Adv2013; 3: 13811–13817.
28.
DineshkumarSMuthusamyAChandrasekaranJ. Temperature and frequency-dependent dielectric properties of electrically conducting oxidatively synthesized polyazomethines and their structural, optical, and thermal characterizations. J Mol Struct2017; 1128: 730–740.
29.
SakthivelPKannanP. Investigation on thermotropic liquid crystalline and photocrosslinkable polyarylidene aryl phosphate esters containing cyclohexanone units. Polymer2005; 46: 9821–9830.
30.
TurnerBLMahieuNCondronLM. Phosphorus-31 nuclear magnetic resonance spectral assignments of phosphorus compounds in soil NaOH–EDTA extracts. Soil Sci Soc Am J2003; 67: 497–510.
31.
RafieeZMallakpourSHatamvandR. Preparation and characterization of heat-resistant polyimide/titanium dioxide nanocomposite films containing triptycene side units by sol-gel processes. High Perform Polym2014; 26: 373–380.
32.
SenolDKayaI. Synthesis and characterization of azomethine oligomers containing ether and ester groups. J Saudi Chem Soc2017; 21: 505–516.
33.
RanganathanTBeaulieuMZilbermanJ. Thermal degradation of deoxybenzoin polymers studied by pyrolysis-gas chromatography/mass spectrometry. Polym Degrad Stabil2008; 93: 1059–1066.
34.
SherrAEGillhamHCKleinHG. Fire retardants for thermoplastics. Adv Chem1968: 307–317.
35.
WangBCLiaoHRYehHC, et al.Theoretical investigation of stokes shift of 3,4-diaryl substituted maleimide fluorophores. J Lumin2005; 113: 321–328.
36.
AnsariMBeraRMondalS, et al.Triptycene-derived photoresponsive fluorescent azo-polymer as chemosensor for picric acid detection. ACS Omega2019; 4: 9383−9392.
37.
DineshkumarSMuthusamyA. Synthesis and spectral characterization of cross linked rigid structured schiff base polymers: effect of substituent position changes on optical, electrical and thermal properties. Polym Plast Technol2016; 55: 368–378.
38.
OterOErtekinKKılıncarslanR, et al.Photo characterization of a novel fluorescent Schiff Base and investigation of its utility as an optical Fe3+ sensor in PVC matrix. Dyes Pigm2007; 74: 730–735.
39.
LiZXZhangLFZhaoWY, et al.Fluoranthene-based pyridine as fluorescent chemosensor for Fe3+. Inorg Chem Commun2011; 14: 1656–1658.
40.
VelmuruganKPrabhuJTangL, et al.A simple chalcone-based fluorescent chemosensor for the detection and removal of Fe3+ ions using a membrane separation method. Anal Methods2014; 6: 2883–2888.
41.
NormayaEBaharuNAAhmadMN. Synthesis of thiosemicarbazone-based colorimetric chemosensor for Cu2+ ions’ recognition in aqueous medium: experimental and theoretical studies. J Mol Struct2020; 1212: 128094.
42.
LakowiczJR. Principles of Fluorescence Spectroscopy. New York: Plenum Press, 1983.
43.
GuoCJiangSZhuW, et al.Polythiophene based fluorescent probe for copper ions with high sensitivity. J Appl Polym Sci2015; 132(1): 42440.
44.
PatilKSMahajanPGPatilSR. Fluorometric detection of Sn2+ ion in aqueous medium using Salicylaldehyde based nanoparticles and application to natural samples analysis. Spectrochim Acta A2017; 170: 131–137.
45.
HeYYinJWangG. New selective “on-off” fluorescence chemosensor based on carbazole Schiff base for Fe3+ detection. Chem Heterocycl Comp2018; 54(2): 146–152.
46.
SahaUCDharaKChattopadhyayB, et al.A new half-condensed schiff base compound: highly selective and sensitive pH-responsive fluorescent sensor. Org Lett2011; 13: 4510–4513.
47.
PallboJSparrEOlssonU. Aggregation behaviour of the amyloid model peptide NACore. Q Rev Biophys2019; 52: 1–10.
48.
HariharanSKarthikeyanB. Optical and surface band bending mediated fluorescence sensing properties of MoS2 quantum dots. RSC Adv2016; 6: 101770–101777.
49.
GautamBPSDaniRKPrasadRL, et al.Synthesis, characterization, single crystal structural studies, antibacterial activity and DFT investigations of 2-chloro-5-ethoxy-3,6-bis(methylamino)-1,4-benzoquinone. Pharm Anal Acta2015; 6(1): 418.
50.
FukuiK. Role of frontier orbitals in chemical reactions. Science1982; 218: 747–754.
51.
AminNAfkhamiAHosseinzadehL, et al.Green and cost-effective synthesis of carbon dots from date kernel and their application as a novel switchable fluorescence probe for sensitive assay of zoledronic acid drug in human serum and cellular imaging. Anal Chim Acta2018; 1030: 183–193.
52.
ShyamalMMazumdarPMaityS, et al.Pyrene scaffold as real time fluorescent Turn-on chemosensor for selective detection of trace level Al(III) and its aggregation induced emission enhancement. J Phys Chem A2016; 120: 210–220.
53.
XuJHHouYMMaQJ, et al.A highly selective fluorescent sensor for Fe3+ based on covalently immobilized derivative of naphthalimide. Spectrochim Acta A Mol Biomol Spectrosc2013; 112: 116–124.
54.
PengH.LCallenderR. Mechanistic analysis of fluorescence quenching of reduced nicotinamide adenine dinucleotide by oxamate in lactate dehydrogenase ternary complexes. Photochem Photobiol2017; 93: 1193–1203.
55.
YangLYangWXuD, et al.A highly selective and sensitive Fe3+ fluorescent sensor by assembling three 1,8-naphthalimide fluorophores with a tris(aminoethylamine), fluorophore. Dyes Pigm2013; 97: 168–174.
56.
ShaktawatVJainNSaxenaR, et al.Temperature dependence of electrical conduction in pure and doped polypyrrole. Polym Bull2006; 57: 535–543.
57.
DoganFTemizkanKKayaI. A novel shape controlled synthesis of bifunctional organic polymeric nanoparticles. Polymer2015; 70: 59–67.
58.
HajdukBWeszkaJJarząbekB, et al. Optical properties of amorphous polyazomethine thin films. J Achiev Mat Manu Eng2007; 24: 67–70.
FanLXuX. A simple strategy to enhance the electrical conductivity of nanotube-conjugate polymer composites via iodine-doping. RSC Adv2015; 95: 78104–78108.
61.
DilekaDDoganFBiliciA, et al.Oxidative synthesis of a novel polyphenol having pendant Schiff base group: synthesis, characterization, non-isothermal decomposition kinetics. Thermochim Acta2011; 518: 72–81.
62.
BazakaKJacobMV. Effects of iodine doping on optoelectronic and chemical properties of polyterpenol thin films. Nanomaterials2017; 11: 11–16.
63.
VimalanMKumarTRTamilselvanS, et al.Growth and properties of novel organic nonlinear optical crystal: l-alaninium tartrate (LAT). Physica B2010; 405: 3907–3913.
64.
WangDDangZM. 12 - Processing of Polymeric Dielectrics for High Energy Density Capacitors. Dielectric Polymer Materials for High-Density Energy Storage. 1st ed. China: Elsevier, 2018, pp. 429–446.
65.
ArjunanSBhaskaranAMohankumarR, et al.Effect of iodic acid dopant on the growth and structural, optical, and electrical properties of l-arginine phosphate single crystals. Mater Manuf Process2012; 27: 49–52.
66.
ManzoorSHusainSSomvanshiA, et al.Investigation of relaxation phenomenon in lanthanum orthoferrite extracted through complex impedance and electric modulus spectroscopy. J Appl Phys2020; 128: 064101.
67.
GowthamBPonnuswamyVPradeeshG. MoO3 overview: hexagonal plate-like MoO3 nanoparticles prepared by precipitation method. J Mater Sci Mater Electron2018; 29: 6835–6843.
Supplementary Material
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
