Research Article
Synthesis of new generation calix[4]arene derivatives as fluorescence chemosensor and its theoretical calculation
Abstract
Calixarenes are among the commonly preferred molecules of the supramolecular chemistry since they are easily synthesizable and functionalizable.In this study, new types of calix[4]aren derivatives containing benzylisoquinoline groups were synthesized and the structures of the obtaining compounds were characterized by spectroscopic techniques such as 1H-NMR, 13C-NMR. Synthesized calix[4]aren derivatives towards some metal cations (Ag+, Al+3, Ba+, Ca+2, Co+2, Cs+2, Fe+3, Hg+2, Li+, Pb+2, Mg+2, Mn+2, Na+, Cu+2, Ba+2, Ni+2, Zn+2, Sr+2 showed fluorescence behaviors ve these behaviors were investigated utilizing UV-vis spectrophotometer and fluorescence spectroscopic techniques.It was found out according to the obtained results that it got complexed in 1:1 ratio as stoichiometric as a result of its activation with aqueous solutions of Cu+2 and Fe+2 ions and responded as an off-on sensor. In this regard, a highly selective and sensitive sensor was developed. Theoretical studies were also conducted in addition to the achieved experimental results. The bonding of metal ions was also calculated theoretically by using Gaussian 09 and GaussView 5.0.8.
Keywords
Thanks
We express our sincere thanks to Assoc. Dr. Murat YILDIZ for helping to use Gaussian 09 and GaussView 5.0.8, to Karamanoglu Mehmetbey University, Faculty of Science, Department of Physics.
References
- [1] Li Q., Guo Y., Shao S., A BODIPY based fluorescent chemosensor for Cu(II) ions and homocysteine/cysteine, Sens. Actuators B: Chem., 171 (2012) 872-877.
- [2] Martinez R., Espinosa A., Tarraga A., Molina P., A new bis(pyrenyl)azadiene-based probe for the colorimetric and fluorescent sensing of Cu(II) and Hg(II), Tetrahedron, 66 (2010) 3662-3667.
- [3] Gao Y., Li Y., Yang X., He F., Huang J., Jiang M., Zhou Z., Chen H., Design, synthesis and biological evaluation of a novel Cu2+ selective fluorescence sensor for bio-detection and chelation, RSC Adv., 5 (2015) 80110–80117.
- [4] Gutsche C.D., Iqbal M., Stewart D., Calixarenes 19 Synthesis Procedures for p-tert Butylcalix[4]arene, J. Org. Chem., 51 (1986) 742.
- [5] Dujols V., Ford F., Czarnik A.W., A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water, J. Am. Chem. Soc., 119 (1997) 7386–7387.
- [6] Xiang Y., Tong A., Jin P., Ju Y., New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity, Org. Lett., 8 (2006) 2863–2866.
- [7] Valeur B., Leray I., Design principles of fluorescent molecular sensors for cation recognition, Coord. Chem. Rev., 205 (2000) 3-40.
- [8] Moczar I., Peragovics A., Baranyai P., Toth K., Huszthy P., Synthesis and fluorescence studies of novel bis(azacrown ether) type chemosensors containing an acridinone unit, Tetrahedron, 66 (2010) 2953-2960.
- [9] Kumar M., Babu J.N., Bhalla V., Kumar R., Ratiometric/on–off sensing of Pb2+ ion using pyrene-appended calix[4]arenes, Sens. Actuators B: Chem., 144 (2010) 183-191.
- [10] Grabchev I., Chevelon J.M., Qian X., Polyamidoamine dendrimer with peripheral 1, 8-naphthalimide groups capable of acting as a PET fluorescent sensor for metal cations, New J. Chem., 27 (2003) 337-340.
- [11] Sivaraman G., Sathiyaraja V., Chellappa D., Turn-on fluorogenic and chromogenic detection of Fe(III) and its application in living cell imaging, J. Lumin., 145 (2014) 480-485.
- [12] Sirilaksanapong S., Sukwattanasinitt M., Rashatasakhon P., 1,3,5-Triphenylbenzene fluorophore as a selective Cu2+ sensor in aqueous media, Chem. Commun., 48 (2012) 293–295.
- [13] Sahin O., Yılmaz M., Synthesis and fluorescence sensing properties of novel pyrene-armed calix[4]arene derivatives, Tetrahedron, 67 (2011) 3501-3508.
- [14] Ocak U., Ocak M., Bartsch R.A., Calixarenes with dansyl groups as potential chemosensors, Inorg. Chim. Acta, 381 (2012) 44-57.
- [15] Tilki T., Sener I., Karcı F., Gulce A., Deligoz H., An approach to the synthesis of chemically modified bisazocalix[4]arenes and their extraction properties, Tetrahedron, 61 (2005) 9624-9629.
- [16] Akkus G.U., Memon S., Sezgin M., Yilmaz M., Synthesis of calix (aza) crown and ıts oligomeric analogue for the extraction of selected metal cations and dichromate anions, Clean—Soil, Air, Water, 37 (2009) 109-114.
- [17] Patra S., Lo R., Chakrabort A., Gunupuru R., Maity D., Ganguly B., Paul P., Calix[4]arene based fluorescent chemosensor bearing coumarin as fluorogenic unit: synthesis, characterization, ion-binding property and molecular modeling, Polyhedron, 50 (2013) 592-601.
- [18] Erdemir S., Tabakci B., Tabakci M.A., Highly selective fluorescent sensor based on calix[4]arene appended benzothiazole units for Cu2+, S2− and HSO4− ions in aqueous solution, Sens. Actuators B: Chem., 228 (2016) 109-116.
- [19] Kumar R., Bhalla V., Kumar M., Cu2+ and CN− selective fluorogenic sensors based on pyrene - appended thiacalix[4]arenes, Tetrahedron, 64 (2008) 8095-8101.
- [20] Bayrakci M., Ertul S., Yilmaz M., Synthesis of di-Substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions, Tetrahedron, 65 (2009) 7963-7968.
- [21] Frisch M.J.E.A., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Nakatsuji H. Gaussian 09, Gaussian Inc., Wallingford CT, 2009; pp 200.
- [22] Deligoz H., Ercan N., The synthesis of some new derivatives of calix[4]arene containing azo groups, Tetrahedron, 58 (2002) 2881-2884.
- [23] Vysotsky O.M., Bohmer V., Wurthner F., Calix[4]arene-functionalized naphthalene and perylene imide dyes, Org. Lett., 4 (2002) 2901-2904.
- [24] Foresman J.B., Frish E., Exploring chemistry with electronic structure methods, Gaussian, Inc., Pittsburgh PA, USA, 1996; pp 253.
- [25] Habib U., Anwar-Ul-Haq A.S., Salma B., Khurshid A., DFT study of polyaniline NH3, CO2, and CO gas sensors: comparison with recent experimental data, J. Phys. Chem. C, 117 (2003) 23701–23711.
- [26] Habib U., Anwar-Ul-Haq A.S., Salma B., Khurshid A., Doping and dedoping processes of polypyrrole: DFT study with hybrid functionals, J. Phys. Chem. C, 118 (2014) 17819–17830.
- [27] Lee M.H., Quang D.T., Jung H.S., Yoon J., Lee C.H., Kim J.S., Ion ınduced FRET on-off in fluorescent calix[4]arene, J. Org. Chem., 72 (2007)4242-4245.
Year 2020,
, 122 - 130, 22.03.2020
Abstract
References
- [1] Li Q., Guo Y., Shao S., A BODIPY based fluorescent chemosensor for Cu(II) ions and homocysteine/cysteine, Sens. Actuators B: Chem., 171 (2012) 872-877.
- [2] Martinez R., Espinosa A., Tarraga A., Molina P., A new bis(pyrenyl)azadiene-based probe for the colorimetric and fluorescent sensing of Cu(II) and Hg(II), Tetrahedron, 66 (2010) 3662-3667.
- [3] Gao Y., Li Y., Yang X., He F., Huang J., Jiang M., Zhou Z., Chen H., Design, synthesis and biological evaluation of a novel Cu2+ selective fluorescence sensor for bio-detection and chelation, RSC Adv., 5 (2015) 80110–80117.
- [4] Gutsche C.D., Iqbal M., Stewart D., Calixarenes 19 Synthesis Procedures for p-tert Butylcalix[4]arene, J. Org. Chem., 51 (1986) 742.
- [5] Dujols V., Ford F., Czarnik A.W., A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water, J. Am. Chem. Soc., 119 (1997) 7386–7387.
- [6] Xiang Y., Tong A., Jin P., Ju Y., New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity, Org. Lett., 8 (2006) 2863–2866.
- [7] Valeur B., Leray I., Design principles of fluorescent molecular sensors for cation recognition, Coord. Chem. Rev., 205 (2000) 3-40.
- [8] Moczar I., Peragovics A., Baranyai P., Toth K., Huszthy P., Synthesis and fluorescence studies of novel bis(azacrown ether) type chemosensors containing an acridinone unit, Tetrahedron, 66 (2010) 2953-2960.
- [9] Kumar M., Babu J.N., Bhalla V., Kumar R., Ratiometric/on–off sensing of Pb2+ ion using pyrene-appended calix[4]arenes, Sens. Actuators B: Chem., 144 (2010) 183-191.
- [10] Grabchev I., Chevelon J.M., Qian X., Polyamidoamine dendrimer with peripheral 1, 8-naphthalimide groups capable of acting as a PET fluorescent sensor for metal cations, New J. Chem., 27 (2003) 337-340.
- [11] Sivaraman G., Sathiyaraja V., Chellappa D., Turn-on fluorogenic and chromogenic detection of Fe(III) and its application in living cell imaging, J. Lumin., 145 (2014) 480-485.
- [12] Sirilaksanapong S., Sukwattanasinitt M., Rashatasakhon P., 1,3,5-Triphenylbenzene fluorophore as a selective Cu2+ sensor in aqueous media, Chem. Commun., 48 (2012) 293–295.
- [13] Sahin O., Yılmaz M., Synthesis and fluorescence sensing properties of novel pyrene-armed calix[4]arene derivatives, Tetrahedron, 67 (2011) 3501-3508.
- [14] Ocak U., Ocak M., Bartsch R.A., Calixarenes with dansyl groups as potential chemosensors, Inorg. Chim. Acta, 381 (2012) 44-57.
- [15] Tilki T., Sener I., Karcı F., Gulce A., Deligoz H., An approach to the synthesis of chemically modified bisazocalix[4]arenes and their extraction properties, Tetrahedron, 61 (2005) 9624-9629.
- [16] Akkus G.U., Memon S., Sezgin M., Yilmaz M., Synthesis of calix (aza) crown and ıts oligomeric analogue for the extraction of selected metal cations and dichromate anions, Clean—Soil, Air, Water, 37 (2009) 109-114.
- [17] Patra S., Lo R., Chakrabort A., Gunupuru R., Maity D., Ganguly B., Paul P., Calix[4]arene based fluorescent chemosensor bearing coumarin as fluorogenic unit: synthesis, characterization, ion-binding property and molecular modeling, Polyhedron, 50 (2013) 592-601.
- [18] Erdemir S., Tabakci B., Tabakci M.A., Highly selective fluorescent sensor based on calix[4]arene appended benzothiazole units for Cu2+, S2− and HSO4− ions in aqueous solution, Sens. Actuators B: Chem., 228 (2016) 109-116.
- [19] Kumar R., Bhalla V., Kumar M., Cu2+ and CN− selective fluorogenic sensors based on pyrene - appended thiacalix[4]arenes, Tetrahedron, 64 (2008) 8095-8101.
- [20] Bayrakci M., Ertul S., Yilmaz M., Synthesis of di-Substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions, Tetrahedron, 65 (2009) 7963-7968.
- [21] Frisch M.J.E.A., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Nakatsuji H. Gaussian 09, Gaussian Inc., Wallingford CT, 2009; pp 200.
- [22] Deligoz H., Ercan N., The synthesis of some new derivatives of calix[4]arene containing azo groups, Tetrahedron, 58 (2002) 2881-2884.
- [23] Vysotsky O.M., Bohmer V., Wurthner F., Calix[4]arene-functionalized naphthalene and perylene imide dyes, Org. Lett., 4 (2002) 2901-2904.
- [24] Foresman J.B., Frish E., Exploring chemistry with electronic structure methods, Gaussian, Inc., Pittsburgh PA, USA, 1996; pp 253.
- [25] Habib U., Anwar-Ul-Haq A.S., Salma B., Khurshid A., DFT study of polyaniline NH3, CO2, and CO gas sensors: comparison with recent experimental data, J. Phys. Chem. C, 117 (2003) 23701–23711.
- [26] Habib U., Anwar-Ul-Haq A.S., Salma B., Khurshid A., Doping and dedoping processes of polypyrrole: DFT study with hybrid functionals, J. Phys. Chem. C, 118 (2014) 17819–17830.
- [27] Lee M.H., Quang D.T., Jung H.S., Yoon J., Lee C.H., Kim J.S., Ion ınduced FRET on-off in fluorescent calix[4]arene, J. Org. Chem., 72 (2007)4242-4245.
There are 27 citations in total.
Details
| Primary Language | English |
|---|---|
| Journal Section | Natural Sciences |
| Authors | |
| Publication Date | March 22, 2020 |
| Submission Date | June 1, 2019 |
| Acceptance Date | October 25, 2019 |
| Published in Issue | Year 2020 |