A novel Schiff base derivative L
(N1-(thiophene-2-ylmethylene)benzene-1,2-diamine) was synthesized via condensation
reaction of 3-thiophene carboxaldehyde and 1,2-diamino benzene. The synthesized compound
was authenticated using 1 H NMR, 13 C NMR, HRMS, and IR
spectroscopy. The compound L was found to be a Fe3+ sensor with
the complexation ratio of 1 : 3 as revealed by Job’s plot with maximum absorption at
318 nm. The photophysical properties were studied using absorption and emission spectra.
DFT and TD-DFT studies were carried out in order to support the photophysical outcomes of
compound L. An antioxidant behaviour of compound L was studied
using TAC, FRAP, and DPPH assays and it was found to be showing better TAC activity than
the used standard i.e. gallic acid.
Yoon
J. and CzarnikA.,
(a) Fluorescent chemosensors of carbohydrates. A means of chemically
communicating the binding of polyols in water based on chelation-enhanced
quenching, Journal of the American Chemical Society114(14) (1992),
5874–5875. Available: 10.1021/ja00040a067.
2.
de
SilvaA.et al., (b) Signaling Recognition Events with Fluorescent
Sensors and Switches, Chemical Reviews97(5) (1997),
1515–1566. Available: 10.1021/cr960386p.
3.
NolanE. and LippardS.,
(c) Tools and Tactics for the Optical Detection of Mercuric
Ion, Chemical Reviews108(9) (2008),
3443–3480. Available: 10.1021/cr068000q.
4.
BoeningD.,
(a) Ecological effects, transport, and fate of mercury: a general
review, Chemosphere40(12) (2000),
1335–1351. Available: 10.1016/s0045-6535(99)00283-0.
5.
YardimM.BudinovaT.EkinciE.PetrovN.RazvigorovaM. and
MinkovaV.,
(b) Removal of mercury (II) from aqueous solution by activated carbon
obtained from furfural, Chemosphere52(5) (2003),
835–841. Available: 10.1016/s0045-6535(03)00267-4.
6.
KerstingB.,
Book Review: The Biological Chemistry of the Elements The inorganic
chemistry of life 243 by J. J. R. Fraústo da Silva and R. J. P.
Williams, ChemBioChem3(11) (2002),
1156–1157, Available: 10.1002/1439-7633(20021104)3:11<1156::aid-cbic1156>3.0.co;2-c.
7.
OhashiA., ItoH.,
KanaiC., ImuraH.
and OhashiK.,
Cloud point extraction of iron(III) and vanadium(V) using 8-quinolinol
derivatives and Triton X-100 and determination of 10–7 mol dm–3
level iron(III) in riverine water reference by a graphite furnace atomic absorption
spectroscopy, Talanta65(2) (2005),
525–530. Available: 10.1016/j.talanta.2004.07.018 [Accessed 7 September 2022].
8.
LunvongsaS., OshimaM., MotomizuS.,
Determination of total and dissolved amount of iron in water samples
using catalytic spectrophotometric flow injection analysis,
Talanta68(3) (2006),
969–973. Available: 10.1016/j.talanta.2005.06.067.
9.
BobrowskiA., NowakK., Zarębski
J., Application of a
bismuth film electrode to the voltammetric determination of trace iron using a
Fe(III)–TEA–BrO3–catalytic system, Analytical and Bioanalytical
Chemistry382(7) (2005),
1691–1697. Available: 10.1007/s00216-005-3313-2.
10.
BagB., PalA.,
Rhodamine-based probes for metal ion-induced chromo-/fluorogenic dual
signaling and their selectivity towards Hg(ii) ion,
Organic&Biomolecular Chemistry9(12) (2011), 4467. Available:
10.1039/c0ob01179g.
11.
SandhuN., et
al., (a) Turn-On” Sensing Behaviour of an In Situ Generated
Fluorescein-Based Probe and Its Preferential Selectivity of Sodium Hypochlorite over
tert -Butyl Hydroperoxide in Lung Adenocarcinoma Cells”,
Chemistry Select5(4) (2020),
1264–1268. Available: 10.1002/slct.201903843.
12.
FengL.ChenZ.
and WangD., (b)
Selective sensing of Fe3+ based on fluorescence quenching by
2,6–bis(benzoxazolyl)pyridine with β-cyclodextrin in neutral aqueous
solution, Spectrochimica Acta Part A: Molecular and Biomolecular
Spectroscopy66(3) (2007),
599–603. Available: 10.1016/j.saa.2006.03.039.
13.
GrabchevI., ChovelonJ., PetkovC., An
iron(III) selective dendrite chelator based on polyamidoamine dendrimer modified with
4-bromo-1,8-naphthalimide, Spectrochimica Acta Part A: Molecular
and Biomolecular Spectroscopy69(1) (2008),
100–104. Available: 10.1016/j.saa.2007.03.014.
14.
ZhangL., FanJ.,
PengX.,
X-ray crystallographic and photophysical properties of rhodamine-based
chemosensor for Fe3+, Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy73(2) (2009),
398–402. Available: 10.1016/j.saa.2009.02.045.
15.
BricksJ., et
al., On the Development of Sensor Molecules that Display
FeIII-amplified Fluorescence, Journal of the American Chemical
Society127(39) (2005),
13522–13529. Available: 10.1021/ja050652t.
16.
SahooS., BeraR.,
BaralM., KanungoB.,
Excited state intramolecular proton transfer (ESIPT) in a dioxotetraamine
derived Schiff base and its complexation with Fe(III) and Cr(III),
Journal of Photochemistry and Photobiology A: Chemistry188(2–3) (2007),
298–310. Available: 10.1016/j.jphotochem.2006.12.027.
17.
ZhangX., ShiraishiY., HiraiT., A new
rhodamine-based fluorescent chemosensor for transition metal cations synthesized by
one-step facile condensation, Tetrahedron Letters48(31) (2007),
5455–5459. Available: 10.1016/j.tetlet.2007.05.171.
18.
JungH., SinghN., JangD.,
Highly Fe3+ selective ratiometric fluorescent probe based on imine-linked
benzimidazole, Tetrahedron Letters49(18) (2008),
2960–2964. Available: 10.1016/j.tetlet.2008.03.002.
19.
PathakR., DessingouJ., HingeV., ThawariA., BasuS.,
RaoC.,
Quinoline Driven Fluorescence Turn On 1,3-Bis-calix[4]arene
Conjugate-Based Receptor to Discriminate Fe3+ from Fe2+,
Analytical Chemistry85(7) (2013),
3707–3714. Available: 10.1021/ac400059w.
20.
ChereddyN.,
Anaphthalimide based PET probe with Fe3+ selective detection ability:
theoretical and experimental study, The Analyst139(24) (2014),
6352–6356. Available: 10.1039/c4an01528b.
21.
JanakipriyaS.,
ChereddyN., KorrapatiP., ThennarasuS., MandalA.,
Selective interactions of trivalent cations Fe3+, Al3+and Cr3+turn on
fluorescence in a naphthalimide based single molecular probe,
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy153 (2016), 465–470.
Available: 10.1016/j.saa.2015.08.044.
22.
HuZ., et al.,
Fe3+-selective fluorescent probe based on rhodamine B and its application
in bioimaging, Sensors and Actuators B: Chemical156(1) (2011),
428–432. Available: 10.1016/j.snb.2011.04.075.
23.
DiwanU., KumarA., KumarV., UpadhyayK.,
Solvent viscosity tuned highly selective NIR and ratiometric fluorescent
sensing of Fe3+ by a symmetric chalcone analogue, Dalton
Transactions42(38) (2013), 13889.
Available: 10.1039/c3dt50733e.
24.
YangY., YuK.,
YangL., LiuJ.,
LiK., LuoS.,
One Single Molecule as a Multifunctional Fluorescent Probe for
Ratiometric Sensing of Fe3+, Cr3+and Colorimetric Sensing of Cu2+,
Sensors15(1) (2014),
49–58. Available: 10.3390/s150100049.
25.
HuS., ZhangS., GaoC.,
XuC., GaoQ.,
A new selective fluorescent sensor for Fe3+ based on a pyrazoline
derivative, Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy113 (2013), 325–331.
Available: 10.1016/j.saa.2013.04.118.
26.
TumambacG., RosencranceC., WolfC.,
Selective metal ion recognition using a fluorescent 1,8-
diquinolylnaphthalene-derived sensor in aqueous solution,
Tetrahedron60(49) (2004),
11293–11297. Available: 10.1016/j.tet.2004.07.053.
27.
AisenP.Wessling-ResnickM.LeiboldE.,
(a) Iron metabolism, Current Opinion in Chemical
Biology3(2) (1999),
200–206. Available: 10.1016/s1367-5931(99)80033-7.
28.
EisensteinR.,
(b) Iron Regulatory Proteins and the Molecular Control of Mammalian Iron
Metabolism, Annual Review of Nutrition20(1) (2000),
627–662. Available: 10.1146/annurev.nutr.20.1.627.
29.
TouatiD.,
Iron and Oxidative Stress in Bacteria,” Archives
of Biochemistry and Biophysics373(6) (2000),
1–6. Available: 10.1006/abbi.1999.1518.
30.
GrabchevI., ChovelonJ., PetkovC., An
iron(III) selective dendrite chelator based on polyamidoamine dendrimer modified with
4-bromo-18-naphthalimide, Spectrochimica Acta Part A: Molecular
and Biomolecular Spectroscopy69(1) (2008),
100–104. Available: 10.1016/j.saa.2007.03.014.
31.
LeeM., GiapT.,
KimS., LeeY.,
KangC., KimJ.,
A novel strategy to selectively detect Fe(iii) in aqueous media driven by
hydrolysis of a rhodamine 6G Schiff base, Chem. Commun.
46(9) (2010),
1407–1409. Available: 10.1039/b921526c [Accessed 7 September 2022].
32.
MuraleD., et
al., Novel molecular tools to discriminate Fe3+ and Fe2+ by
fluorescence via turn-on” responses within neuronal cells,
Sensors and Actuators B: Chemical185 (2013), 755–761.
Available: 10.1016/j.snb.2013.05.019.
33.
SinghA.,
Anovel, selective, and extremely responsive thienyl-based dual
fluorogenic probe for tandem superoxide and Hg2+chemosensing,
Dalton Trans. 42(10)
(2013), 3285–3290. Available: 10.1039/c2dt32135a.
34.
SinghA.,
Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom
turn-on and H2O2 neuronal system probing, Chemical
Communications48(58) (2012), 7298.
Available: 10.1039/c2cc33076h.
35.
SandhuN.,
Experimental and theoretical observations of alkylated EOSIN based
turn-on” superoxide sensor as well as its anti-microbial study,
Main Group Chemistry20(4) (2021),
623–632. Available: 10.3233/mgc-210068.
36.
UddinS., AliM.,
YesminM.,
Antioxidant and Antibacterial Activities of Senna
toraRoxb., American Journal of Plant Physiology3(2) (2008),
96–100. Available: 10.3923/ajpp.2008.96.100.
37.
KalitaP., TapanB., PalT.,
KalitaR.,
Estimation Of Total Flavonoids Content (Tfc) And Antioxidant Activities
Of Methanolic Whole Plant Extract Of Biophytum Sensitivum Linn,
Journal of Drug Delivery and Therapeutics3(4) (2013). Available: 10.22270/jddt.v3i4.546.
38.
BenzieI., StrainJ.,
The Ferric Reducing Ability of Plasma (FRAP) as a Measure of Antioxidant
Power”: The FRAP Assay, Analytical Biochemistry239(1) (1996),
70–76. Available: 10.1006/abio.1996.0292.
39.
PrietoP., PinedaM., AguilarM.,
Spectrophotometric Quantitation of Antioxidant Capacity through the
Formation of a Phosphomolybdenum Complex: Specific Application to the Determination of
Vitamin E, Analytical Biochemistry269(2) (1999),
337–341. Available: 10.1006/abio.1999.4019.
40.
SahooS., SharmaD., BeraR.,
CrisponiG., CallanJ.,
Iron(iii) selective molecular and supramolecular fluorescent
probes, Chemical Society Reviews41(21) (2012), 7195.
Available: 10.1039/c2cs35152h.
41.
LiuQ., et al.,
Fluorescent Carbon Dots as Nanosensors for Monitoring and Imaging Fe3+
and [HPO4]2–Ions, ACS Applied Nano Materials4(1) (2020),
190–197. Available: 10.1021/acsanm.0c02515.
42.
Annie
HoJ., ChangH., SuW.,
DOPA-Mediated Reduction Allows the Facile Synthesis of Fluorescent Gold
Nanoclusters for Use as Sensing Probes for Ferric Ions,
Analytical Chemistry84(7) (2012),
3246–3253. Available: 10.1021/ac203362g.
43.
DongX., WangR.,
WangJ., ZangS.,
MakT.,
Highly selective Fe3+ sensing and proton conduction in awater-stable
sulfonate–carboxylate Tb–organic-framework, Journal of Materials
Chemistry A3(2) (2015),
641–647. Available: 10.1039/c4ta04421e.
44.
LiS., LiY.,
CaoJ., ZhuJ.,
FanL., LiX.,
Sulfur-Doped Graphene Quantum Dots as a Novel Fluorescent Probe for
Highly Selective and Sensitive Detection of Fe3+, Analytical
Chemistry86(20) (2014),
10201–10207. Available: 10.1021/ac503183y.
KoopmansT.,
Über die Zuordnung von Wellenfunktionen und Eigenwertenzu den Einzelnen
Elektronen Eines Atoms, Physica1(1–6) (1934),
104–113. Available: 10.1016/s0031-8914(34)90011-2.
47.
SharmaA., CannooD.,
Effect of extraction solvents/techniques on polyphenolic contents and
antioxidant potential of the aerial parts of Nepeta leucophylla and the analysis of
their phytoconstituents using RP-HPLC-DAD and GC-MS, RSC
Advances6(81) (2016),
78151–78160. Available: 10.1039/c6ra12038e.
