SYNTHESIS OF CYCLEN BODIPY DYAD AND ITS METAL COMPLEXES: EVALUATION OF ANION RECOGNITION FEATURES

Yıl 2019, Cilt: 5 Sayı: 1, 69 - 99, 30.06.2019

Fatih Algı , Serkan Karakaya

https://doi.org/10.22531/muglajsci.512383

Öz

In this study, a new compound, viz. 4,4-Difluoro-8-(1,4,7,10-tetraazacyclododecane)methyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1), and its metal complexes (1-Zn,1-Cu,and 1-Ni) are synthesized and spectroscopically characterized (UV-Vis, luminescence-fluorescence, NMR, FTIR, and MS). Anion sensing properties of compound 1and its metal complexes (1-Zn,1-Ni and1-Cu) are tested in the presence of various anionic species in acetonitrile media. Fluorescence measurements indicated that, 1-Ni and1-Cu do not have any selectivity towards various anions except weak interactions.On the other hand1-Znshows good response and selectivity toward acetate ion based on fluorescence enhancement. In addition, JOB studies demonstrate that the interaction between 1-Znand acetate ion were with a ratio of 1:2 and limit of detection (LOD) of 1-Znwas calculated as 4.76x10^-6M for acetate ion detection. Moreover, 1-Znprovides a certain change in color in the presence of acetate. The results demonstrate that 1-Zncan be utilized for fluorogenic and naked eye detection of acetate anion.

Anahtar Kelimeler

BODIPY, Cyclen, Acetate Ion, Zinc(II)

Kaynakça

• [1] Goswami, S. and Chakrabarty, R., "Cu(II) Complex Of An Abiotic Receptor As Highly Selective Fluorescent Sensor For Acetate", Tetrahedron Letters, 50, 5994-5997, 2009. [2] Algi, M.P., "A Fluorescent Hypochlorite Probe Built On 1,10-Phenanthroline Scaffold And Its Ion Recognition Features", Journal of Fluorescence, 26, 487-496, 2016.[3] Algi, M.P., "A Highly Selective Dual Channel Hypochlorite Probe Based On Fluorescein And 1,10-Phenanthroline", Tetrahedron, 72, 1558-1565, 2016.[4] Hosseini, M., Ganjali, M.R., Veismohammadi, B., Faridbod, F., Abkenar, S.D. and Niasari, M. S., "Selective recognition of acetate ion based on fluorescence enhancement chemosensor", Luminescence, 27, 341-345, 2012.[5] Shang, X., Tian, S., Xi, N., Li, Y., Liang, D., Liu, Y., Yin, Z., Zhang, J. and Xu, X., "Colorimeric And Fluorescence On–Off Probe For Acetate Anion Based On Thiourea Derivative: Theory And Experiment" Spectrochimica Acta Part A, 103, 276–281, 2013.[6] Tavallali, H., Rad, G.D., Parhami, A. and Abbasiyan, E., "A New Application Of Bromopyrogallol Red As A Selective And Sensitive Competition Assay For Recognition And Determination Of Acetate Anion In DMSO/Water Media", Dyes and Pigments, 94, 541-547, 2012.[7] Huang, W., Lin, H. and Lin, H., "Fluorescent Acetate-Sensing In Aqueous Solution", Sensors and Actuators B Chemical, 153, 404-408, 2011.[8] Liu, G. and Shao, J., "Ratiometric Fluorescence And Colorimetric Sensing Of Anion Utilizing Simple Schiff Base Derivatives", Journal of Inclusion Phenomena and Macrocyclic Chemistry, 76, 99-105, 2013.[9] Kumar, S., Singh, P. and Kumar, S., "1-(2-Naphthalenyl)Benzimidazolium Based Fluorescent Probe For Acetate Ion In 90% Aqueous Buffer" Tetrahedron Letters, 53, 2248-2252, 2012.[10] Feng, M., Jiang, X., Dong, Z., Zhang, D., Wang, B. and Gao, G., "Selective Recognition Of Acetate Ion By Perimidinium-Based Receptors", Tetrahedron Letters, 53, 6292-6296, 2012.[11] Goswami, S., Maity, S., Das, A.K. and Maity, A.C., "Single Chemosensor For Highly Selective Colorimetric And Fluorometric Dual Sensing Of Cu(II) As Well As ‘Nirf’ To Acetate Ion", Tetrahedron Letters, 54, 6631-6634, 2013.[12] Kumar, M.S., Kumar, S.L. and Sreekanth, A., "An Efficient Triazole-Based Fluorescent “Turn-On” Receptor For Naked-Eye Recognition Of F− And AcO−: Uv–Visible, Fluorescence And 1H NMR Studies", Material Science and Engineering C, 33, 3346-3352, 2013.[13] Xu, K., Kong, H., Li, Q., Song, P., Dai, Y. and Yang, L., "Novel Anthracene-Based Fluorescent Sensor For Selective Recognition Of Acetate Anions In Protic Media", Spectrochimica Acta Part A, 137, 957-961, 2015.[14] Sharma, D., Kuba, A., Thomas, R., Kumar, S.K.A., Kuwar, A., Choi, H., J. and Sahoo, S.K., "Acetate Selective Fluorescent Turn-On Sensors Derived Using Vitamin B6 Cofactor Pyridoxal-5-Phosphate", Spectrochimica Acta Part A, 157, 110-115, 2016.[15] Liu, G. and Shao, J., "Selective Ratiometric Fluorescence Detection Of Acetate Based On A Novel Schiff Base Derivative", Journal of Fluorescence, 22, 397-401, 2012.[16] Hu, Z., Q., Wang, X.M., Feng, Y.C., Ding, L., Li, M. and Lin, C.S., "A Novel Colorimetric And Fluorescent Chemosensor For Acetate Ions In Aqueous Media Based On A Rhodamine 6g–Phenylurea Conjugate In The Presence Of Fe(III) Ions", Chemistry Communications, 47, 1622-1624, 2011.[17] Shang, X., Yuan, J., Du, Z., Wang, Y., Jia, S., Han, J., Li, Y., Zhang, J. and Xu, X., "Determination Limit Of Fluorescence Turn‐On Probes For The Acetate Anion", Helvetica Chimica Acta, 96, 719-731, 2013.[18] Bhuyan, M., Katayev, E., Stadlbauer, S., Nonaka, H., Ojida, A., Hamachi, I. and König, B., "Rigid Luminescent Bis‐Zinc(Ii)–Bis‐Cyclen Complexes For The Detection Of Phosphate Anions And Non‐Covalent Protein Labeling In Aqueous Solution", European Journal of Organic Chemistry, 2807-2817, 2011.[19] Li, S., Chen, J.X., Xiang, Q.X., Zhang, L.Q., Zhou, C., H., Xie, J.Q., Yu, L. and Li, F.Z., "The Synthesis And Activities Of Novel Mononuclear Or Dinuclear Cyclen Complexes Bearing Azole Pendants As Antibacterial And Antifungal Agents", European Journal of Medicinal Chemistry, 84, 677-686, 2014.[20] Aoki, S., Jikiba, A., Takeda, K. and Kimura, E., "A Zinc(II) Complex-Conjugated Polymer For Selective Recognition And Separation Of Phosphates", Journal of Physical Organic Chemistry, 17, 89-497, 2004.[21] Gruber, B., Stadlbauer, S., Woinaroschy, K. and König, B., "Luminescent Vesicular Receptors For The Recognition Of Biologically Important Phosphate Species", Organic & Biomolecular Chemistry, 8, 3704-3714, 2010.[22] Huang, X.H., Lu, Y., He, Y.B. and Chen, Z.H., "A Metal–Macrocycle Complex As A Fluorescent Sensor For Biological Phosphate Ions In Aqueous Solution" European Journal of Organic Chemistry, 1921-1927, 2010.[23] Jose, D.A., Stadlbauer, S. and König, B., "Polydiacetylene‐Based Colorimetric Self‐Assembled Vesicular Receptors For Biological Phosphate Ion Recognition", Chemistry - A European Journal, 1, 7404-7412, 2009.[24] Du. J., Wang, X., Jia, M., Li, T., Mao, J. and Guo, Z., "Recognition Of Phosphate Anions In Aqueous Solution By A Dinuclear Zinc(II) Complex Of A Cyclen-Tethered Terpyridine Ligand", Inorganic Chemistry Communications, 11, 999-1002, 2008.[25] Siters, K.E., Sander, S.A., Devlin, J.R. and Morrow, J.R., "Bifunctional Zn(II) Complexes For Recognition Of Non-Canonical Thymines In Dna Bulges And G-Quadruplexes", Dalton Transactions, 44, 3708-3716, 2015.[26] del Mundo, I.M.A., Siters, K.E., Fountain, M.A. and Morrow, J.R., "Structural Basis For Bifunctional Zinc(II) Macrocyclic Complex Recognition Of Thymine Bulges In DNA", Inorganic Chemistry, 51, 5444-5457, 2012.[27] Kimura, E., Kikcuhi, M., Kitamura, H. and Koike, T., "Selective And Efficient Recognition Of Thymidylylthymidine (Tpt) By Bis(Znii‐Cyclen) And Thymidylylthymidylylthymidine (Tptpt) By Tris(Znii‐Cyclen) At Neutral pH In Aqueous Solution", Chemistry A European Journal, 5(11), 3113-3123, 1999.[28] Micoli, A., Soriano, M.L., Traboulsi, H., Quintana, M. and Prato, M., "ZnII‐Cyclen As A Supramolecular Probe For Tagging Thymidine Nucleosides On Carbon Nanotubes", European Journal of Organic Chemistry, 18, 3685-3690, 2013.[29] Zheng, Z. and Spiccia, L., "OFF–ON Fluorescent Detection Of Thymidine Nucleotides By A Zinc(II)–Cyclen Complex Bearing Two Diagonal Pyrenes", Chemistry A European Journal, 15, 12941-12944, 2009.[30] Gruber, B., Kataev, E., Aschenbrenner, J., Stadlbuer, S. and König, B., "Vesicles And Micelles From Amphiphilic Zinc(II)–Cyclen Complexes As Highly Potent Promoters Of Hydrolytic DNA Cleavage", Journal of American Chemical Society, 133, 20704-20707, 2011.[31] Kolemen, S. and Akkaya, E.U., "Reaction-Based BODIPY Probes For Selective Bio-Imaging", Coordination Chemistry Reviews, 354, 121-134, 2018.[32] Laudet, A. and Burgess, K., "BODIPY Dyes And Their Derivatives:  Syntheses And Spectroscopic Properties", Chemical Reviews, 107, 4891-4932, 2007.[33] Ulrich, G. and Ziessel, R., "The Chemistry Of Fluorescent Bodipy Dyes: Versatility Unsurpassed", Angewandte Chemie International Edition, 47, 1184-1201, 2008.[34] Antina, E.V., Bumagina, N.A., V’yugin, A.I. and Solomonov, A.V., "Fluorescent Indicators Of Metal Ions Based On Dipyrrоmethene Platform", Dyes and Pigments, 136: 368-381, 2017.[35] Lu, H., Mack, J., Nyokong, T., Kobayashi, N., and Shen, Z., "Optically Active BODIPYs", Coordination Chemistry Reviews, 318, 1-15, 2016.[36] Benstead, M., Mehl, G.H. and Boyle, R.W., "4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) As Components Of Novel Light Active Materials", Tetrahedron, 67, 3573-3601, 2011.[37] Guliyev, R., Ozturk, S., Kostereli, Z. and Akkaya, E.U., "From Virtual To Physical: Integration Of Chemical Logic Gates", Angewandte Chemie International Edition, 50, 9826-9831, 2011.[38] Kolemen, S., Işık, M., Kim, G.M., Kim, D., Geng, H., Buyuktemiz, M., Karatas, T., Zhang, X-F., Dede, Y., Yoon, J. and Akkaya, E.U., "Intracellular Modulation Of Excited-State Dynamics In A Chromophore Dyad: Differential Enhancement Of Photocytotoxicity Targeting Cancer Cells", Angewandte Chemie International Edition, 54, 5340-5344, 2015.[39] Degirmenci, A. and Algi, F., "Synthesis, Chemiluminescence And Energy Transfer Efficiency Of 2,3-Dihydrophthalazine-1,4-Dione And BODIPY Dyad", Dyes and Pigments, 140, 92-99, 2017.[40] Karakaya, S. and Algi, F., "A Novel Dual Channel Responsive Zinc(II) Probe", Tetrahedron Letters, 55(40), 5555-5559, 2014.[41] Pamuk, M. and Algi, F., "Synthesis Of A Novel On/Off Fluorescent Cadmium(II) Probe", Tetrahedron Letters, 53(51), 7010-7012, 2012.[42] Ekmekci, Z., "Highly Selective Fluorescence ‘Turn-Off’ Sensors For Cu2+ In Aqueous Environments", Tetrahedron Letters, 56 1878-1881, 2015.[43] Li, Z, Geng, Z.R., Zhang, C., Wang, X.B. and Wang Z.L., "BODIPY-Based Azamacrocyclic Ensemble For Selective Fluorescence Detection And Quantification Of Homocysteine In Biological Applications", Biosensensors and Bioelectronics, 72, 1-9, 2015.[44] Wu, H., Krishnakumar, S., Yu, J., Liang, D., Qi, H., Lee, Z.W., Deng, L.W. and Huang, D., "Highly Selective And Sensitive Near‐Infrared‐Fluorescent Probes For The Detection Of Cellular Hydrogen Sulfide And The Imaging Of H2S In Mice", Chemistry – An Asian Journal, 9, 3604-3611, 2014.[45] Valkova, Y.A., Brizet, B., Harvey, P.D., Averin, A.D., Goze, C. and Denat, F., "BODIPY Dyes Functionalized With Pendant Cyclic And Acyclic Polyamines", European Journal of Organic Chemistry, 2013, 4270-4279, 2013.[46] Valkova, Y.A., Brizet, B., Harvey, P.D., Denat, F and Goze, C., "High Yield SNAr On 8‐Halogenophenyl‐BODIPY With Cyclic And Acyclic Polyamines", European Journal of Organic Chemistry, 2014, 2268-2274, 2014.[47] Wilson, J.M., "Synthesis of Biologically Active Heterocyclic Compounds" PhD Dissertation, University of Glasgow, 2007.[48] Kalai, T. and Hideg, K., "Synthesis Of New, Bodipy-Based Sensors And Labels" Tetrahedron, 62, 10352-10360, 2006.