Araştırma Makalesi
BibTex RIS Kaynak Göster

Cu2+ Iyonlarının Hassas ve Seçici Tayini için Rhodamine B Türevli Etkili Bir 'Off-On' Yapay Prop

Yıl 2020, Cilt: 13 Sayı: 2, 811 - 827, 31.08.2020
https://doi.org/10.18185/erzifbed.735011

Öz

Bu çalışma, Cu2+ iyonlarını seçici bir şekilde tanıma ve ayırt etmek için yeni bir ksanten-temelli kolorimetrik ve floresan ‘on-off’ sensörün sentezini ve optik uygulamasını tanımlamaktadır. Bu sensörün karakterizasyonu, NMR (1H & 13C), FT-IR ve LC-MS/MS analizleri ile yapılmıştır. Test edilen metal iyonları arasından, tampon çozeltisi içerisindeki proba sadece Cu2+ iyonları eklendiğinde, çıplak gözle görülebilen renksiz durumdan mor renge bir dönüşümün takip ettiği absorpsiyon ve floresan emisyonlarında (565 ve 588 nm) maksimum artışlar gözlenmiştir. RhCHN probun başlangıçta kullanılan metal iyonları arasından sadece bakır iyonlarına karşı kaydadeğer bir seçicilik ve duyarlılık gösterdiği bulunmuştur. Job's plot metoduna göre, RhCHN’nin 1:1 koordinasyon stokiyometrisi ile Cu2+ iyonuna bağlandığı tahmin edilmiştir. Daha önceki çalışmalarda vurgulandığı gibi, Cu2+ ile RhCHN arasındaki güçlü bağ etkileşimi muhtemelen halka yapısının açılması üzerinden gerçekleşmektedir. Bakır iyonları için kabul edilebilir bir tayin alt sınırıyla, analitik uygulamalar, kromojenik ve florojenik çifte cevap veren prop RhCHN’nin, sulu ortamdaki Cu2+ iyonlarını direkt görüntüleme ve tayini için etkili bir şekilde kullanılabileceğini göstermiştir.

Kaynakça

  • Adhikari, S., Ta, S., Ghosh, A., Guria, S., Pal, A., Ahir, M., Das, D. 2019. “A 1, 8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ ion in living cells”. Journal of Photochemistry and Photobiology A: Chemistry, 372, 49-58.
  • Chatterjee, N., Mahaling, B., Sivakumar, S., Bharadwaj, P. K. 2016. “A highly selective and sensitive “turn-on” fluorescence chemosensor for the Cu2+ ion in aqueous ethanolic medium and its application in live cell imaging”. Journal of Photochemistry and Photobiology A: Chemistry, 330 (2016), 110-116.
  • Dai, K., Xu, B., Chen, J. 2014. “A Rhodamine-based “off-on” colorimetric and fluorescent chemosensor for Cu (II) in aqueous and non-aqueous media”. Journal of Fluorescence, 24, 1129-1136.
  • Ding, H., Li, B., Pu, S., Liu, G., Jia, D., Zhou, Y. 2017. “A fluorescent sensor based on a diarylethene-rhodamine derivative for sequentially detecting Cu2+ and arginine and its application in keypad lock”. Sensors and Actuators B: Chemical, 247, 26-35.
  • Ding, J., Yuan, L., Gao, L., Chen, J. 2012. “Fluorescence quenching of a rhodamine derivative: selectively sensing Cu2+ in acidic aqueous media”. Journal of Luminescence, 132, 1987-1993.
  • Dong, M., Ma, T. H., Zhang, A. J., Dong, Y. M., Wang, Y. W., Peng, Y. 2010. “A series of highly sensitive and selective fluorescent and colorimetric “off-on” chemosensors for Cu (II) based on rhodamine derivatives”. Dyes and pigments, 87, 164-172.
  • Franco, L. L., Almeida, M. V. de, Silva, L. F. R. e, Vieira, P. P. R., Pohlit, A. M., Valle, M. S. 2012. “Synthesis and antimalarial activity of dihydroperoxides and tetraoxanes conjugated with bis (benzyl) acetone derivatives”. Chemical biology & drug design, 79, 790-797.
  • Guo, D., Dong, Z., Luo, C., Zan, W., Yan, S., Yao, X. 2014. “A rhodamine B-based “turn-on” fluorescent sensor for detecting Cu 2+ and sulfur anions in aqueous media”. RSC Advances, 4(11), 5718-5725.
  • Hu, J. H., Long, C., Fu, Q. Q., Ni, P. W., Yin., Z. Y. 2019. “A novel highly selective colorimetric and “turn-on” fluorimetric chemosensor for detecting Hg2+ based on Rhodamine B hydrazide derivatives in aqueous media”. Journal of Photochemistry and Photobiology A: Chemistry, 379, 105-111.
  • Hu, Y., Zhang, J., Lv, Y. Z., Huang, X. H., Hu, S. L. 2016. “A new rhodamine-based colorimetric chemosensor for naked-eye detection of Cu2+ in aqueous solution”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 157, 164-169.
  • Hu, Z. Q., Wang, X. M., Feng, Y. C., Ding, L., Lu, H. Y. 2011. “Sulfonyl rhodamine hydrazide: A sensitive and selective chromogenic and fluorescent chemodosimeter for copper ion in aqueous media”. Dyes and Pigments, 88, 257-261.
  • Huo, F., Wang, L., Yin, C. , Yang, Y., Tong, H., Chao, J., Zhang, Y. 2013. “The synthesis, characterization of three isomers of rhodamine derivative and their application in copper (II) ion recognition”. Sensors and Actuators B: Chemical, 188, 735-740.
  • Jiang, Z., Tian, S., Wei, C., Ni, T., Li, Y., Dai, L., Zhang, D. 2013. “A novel selective and sensitive fluorescent turn-on chemodosimeter based on rhodamine hydrazone for copper ions and its application to bioimaging”. Sensors and Actuators B: Chemical, 184, 106-112.
  • Jiao, Y., Liu, X., Zhou, L., He, H., Zhou, P., Duan, C., Peng, X. 2018. “A fluorescein derivative-based fluorescent sensor for selective recognition of copper (II) ions”. Photochemistry and Photobiology A: Chemistry, 355, 67-71.
  • Jiao, Y., Zhou, L., He, H., Yin, J., Gao, Q., Wei, J., Duan, C., Peng, X. 2018. “A novel rhodamine B-based “off-on’’fluorescent sensor for selective recognition of copper (II) ions”. Talanta, 184, 143-148.
  • Kempahanumakkagaari, S. K., Thippeswamy, R., Malingappa, P. 2014. “A new rhodamine B based fluorometric chemodosimeter for Cu2+ ion in aqueous and cellular media”. Journal of Luminescence, 146, 11-17.
  • Li, G., Tao, F., Wang, H., Li, Y., Wang, L. 2015. “A novel reversible colorimetric chemosensor for rapid naked-eye detection of Cu2+ in pure aqueous solution”. Sensor and Actuators B: Chemical. 211, 325-331.
  • Li, K., Xiang, Y., Wang, X., Li, J., R. Hu, A., Tong, Tang, B. Z. 2014. “Reversible photochromic system based on rhodamine B salicylaldehyde hydrazone metal complex”. The Journal of the American Chemical Society, 136, 1643-1649.
  • Li, M., Lv, H. S., Luo, J. Z., Miao, J. Y., Zhao, B. X. 2013. “An effective “turn-on” rodamine-based fluorescent chemosensor for Cu (II) in living cells”. Sensors and Actuators B: Chemical, 188, 1235-1240.
  • Li, P., Zhou, H., Tang, B. 2012. “A lysosomal-targeted fluorescent probe for detecting Cu2+”. Journal of Photochemistry and Photobiology A: Chemistry, 249, 36-40.
  • Li, W., Zhang, Y., Gan, X., Yang, M., Mie, B., Fang, M., Zhang, Q., Yu, J., Wu, J., Tian, Y., Zhou, H. 2015. “A triphenylamine-isophorone-based “off–on” fluorescent and colorimetric probe for Cu2+”. Sensors and Actuators B: Chemical, 206, 640-646.
  • Lou, X., Qiang, L., Qin, J., Li, Z. 2009. “A new rhodamine-based colorimetric cyanide chemosensor: convenient detecting procedure and high sensitivity and selectivity”. ACS Applied Materials & Interfaces, 1, 2529-2535.
  • Lv, L., Diao, Q. 2017. “A highly selective and sensitive rhodamine-derived fluorescent probe for detection of Cu2+”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 179, 221-226.
  • Lv, T., Xu, Y., Li, H., Liu, F., Sun, S. 2018. “A Rhodamine B-based fluorescent probe for imaging Cu2+ in maize roots”. Bioorganic & Medicinal Chemistry Letters, 26, 1448-1452.
  • Mergu, N., Gupta, V. K. 2015. “A novel colorimetric detection probe for copper (II) ions based on a Schiff base”. Sensor and Actuators B: Chemical, 210, 408-417.
  • Min, M., Wang, X., Chen, Y., Wang, L., Huang, H., Shi, J. 2013. “Highly sensitive and selective Cu2+ sensor based on electrospun rhodamine dye doped poly (ether sulfones) nanofibers”. Sensors and Actuators B: Chemical,188, 360-366.
  • Muthuraj, B., Deshmukh, R., Trivedi, V., Iyer, P. K. 2014. “Highly selective probe detects Cu2+ and endogenous no gas in living cell”. ACS Applied Materials & Interfaces, 6, 6562-6569.
  • Nair, R. Raju, R., M., Patel, N. P., Raval, I. H., Suresh, E., Haldar, S., Chatterjee, P. B. 2015. “Naked eye instant reversible sensing of Cu2+ and its in situ imaging in live brine shrimp, artemia”. Analyst. 140, 5464-5468.
  • Ozdemir, M. 2017. “A fast-response, highly selective, chromogenic and fluorescent chemosensor for the detection of Hg2+ ions”. Sensors and Actuators B: Chemical, 249, 217-228.
  • Ozdemir, M. 2019. “A novel chromogenic molecular sensing platform for highly sensitive and selective detection of Cu2+ ions in aqueous environment”. Journal of Photochemistry and Photobiology A: Chemistry, 369, 54-69.
  • Ozdemir, M. 2016. “A rhodamine-based colorimetric and fluorescent probe for dual sensing of Cu2+ and Hg2+ ions”. Journal of Photochemistry and Photobiology A: Chemistry, 318, 7-13, 2016.
  • Puangploy, P., Smanmoo, S., Surareungchai, W. 2014. “A new rhodamine derivative-based chemosensor for highly selective and sensitive determination of Cu2+”. Sensors and Actuators B: Chemical, 193, 679-686
  • Reddy, N.S.K., Badam, R., Sattibabu, R., Molli, M., Muthukumar, V.S., Sai, S.S.S., Rao, G.N. 2014. “Synthesis, characterization and nonlinear optical properties of symmetrically substituted dibenzylideneacetone derivatives”. Chemical Physics Letters, 616 (2014), 142-147.
  • Sahana, S., Mishra, G., Sivakumar, S., Bharadwaj, P. K. 2017. “Highly sensitive and selective “turn-on” chemodosimeter based on Cu2+-promoted hydrolysis for nanomolar detection of Cu2+ and its application in confocal cell imaging”. Journal of Photochemistry and Photobiology A: Chemistry, 334, 47-54.
  • Saleem, M., Lee, K. H. 2014. “Selective fluorescence detection of Cu2+ in aqueous solution and living cells”. Journal of Luminescence, 145, 843-848.
  • Sun, T., Li, Y., Niu, Q., Li, T., Liu, Y. 2018. “Highly selective and sensitive determination of Cu2+ in drink and water samples based on a 1, 8-diaminonaphthalene derived fluorescent sensor”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 198, 142-147.
  • Sun, Z., Li, H., Guo, D., Liu, Y., Tian, Z., Yan, S. 2015. “A novel piperazine-bis (rhodamine-B)-based chemosensor for highly sensitive and selective naked-eye detection of Cu2+ and its application as an INHIBIT logic device”. Journal of Luminescence, 167, 156-162.
  • Tang, L., Guo, J., Wang, N. 2013. “A New Rhodamine B Hydrazide Hydrazone Derivative for Colorimetric and Fluorescent”. Bulletin of the Korean Chemical Society, 34, 159-163.
  • Tang, R., Lei, K., Chen, K., Zhao, H., Chen, J. 2011. “A rhodamine-based off–on fluorescent chemosensor for selectively sensing Cu (II) in aqueous solution”. Journal of Fluorescence, 21, 141-148.
  • Tang, X., Zhu, Z., Wang, Y., Han, J., Ni, L., Wang, L., Zhang, H., Li, J., Qiu, Y. 2018. “A dual site controlled probe for fluorescent monitoring of intracellular pH and colorimetric monitoring of Cu2+”. Sensors and Actuators B: Chemical, 270, 35-44.
  • Udhayakumari, D., Naha, S., Velmathi, S. 2017. “Colorimetric and fluorescent chemosensors for Cu 2+, A comprehensive review from the years 2013–15”. Analytical Methods, 9, 552-578.
  • Wang, J., Li, H., Long, L., Xiao, G., Xie, D. 2012. “Fast responsive fluorescence turn-on sensor for Cu2+ and its application in live cell imaging”. Journal of Lumines cence,132, 2456-2461.
  • Wang, J., Long, L., Xie, D., Song, X. 2013. “Cu2+-selective “Off–On” chemsensor based on the rhodamine derivative bearing 8-hydroxyquinoline moiety and its application in live cell imaging”. Sensors and Actuators B: Chemical, 17, 27-33.
  • Wang, M., Yan, F., Zou, Y., Chen, L., Yang, N., Zhou, X. 2014. “Recognition of Cu2+ and Hg2+ in physiological conditions by a new rhodamine based dual channel fluorescent probe”. Sensor and Actuators B: Chemical, 192, 512-521.
  • Wang, R., Ren, P., Pu, S., Liu, G., Cui, S. 2014. “Novel sensitive sensors for Cu2+ and optical switching of photochromic dithienylethene derivatives”. Journal of Photochemistry and Photobiology A: Chemistry, 294, 44-53.
  • Wang, X., Tao, J., Chen, X., Yang, H. 2017. “An ultrasensitive and selective “off-on” rhodamine-based colorimetric and fluorescent chemodosimeter for the detection of Cu2+”. Sensors and Actuators B: Chemical, 244, 709-716.
  • Wang, Y., Chang, H. Q., Wu, W. N., Mao, X. J., Zhao, X. L., Yang, Y., Jia, L. 2017. “A highly sensitive and selective colorimetric and off–on fluorescent chemosensor for Cu2+ based on rhodamine 6G hydrazide bearing thiosemicarbazide moiety”. Journal of Photochemistry and Photobiology A: Chemistry, 335, 10-16.
  • Wang, Y., Wu, H. Q., Sun, J. H., Liu, X. Y., Luo, J., Chen, M. Q. 2012. “A novel chemosensor based on rhodamine derivative for colorimetric and fluorometric detection of Cu2+ in aqueous solution”. Journal of Fluorescence, 22, 799-805.
  • Wu, S. P., Huang, Z. M., Liu, S. R., Chung, P. K. 2012. “A pyrene-based highly selective turn-on fluorescent sensor for copper (II) ion and its application in live cell imaging”. Journal of Fluorescence, 22, 253-259.
  • Xiang, Y., Tong, A., Jin, P., Ju, Y. 2006. “New fluorescent rhodamine hydrazone chemosensor for Cu (II) with high selectivity and sensitivity”. Organic letters, 8, 2863-2866.
  • Xu, J., Hou, Y., Ma, Q., Wu, X., Feng, S., Zhang, J., Shen, Y. 2014. “A highly selective fluorescent probe for Cu2+ based on rhodamine B derivative”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 124, 416-422.
  • Xu, L., Wei, S., Diao, Q., Ma, P., Liu, X., Sun, Y., Song, D., Wang, X. 2017. “Sensitive and selective rhodamine-derived probes for fluorometric sensing of pH and colorimetric sensing of Cu2+”. Sensors and Actuators B: Chemical, 246, 395-401.
  • Xu, Z., Zhang, L., Guo, R., Xiang, T., Wu, C., Zheng, Z., Yang, F. 2011. “A highly sensitive and selective colorimetric and off–on fluorescent chemosensor for Cu 2+ based on rhodamine B derivative”. Sensors and Actuators B: Chemical, 156, 546-552.
  • Yang, Z., Zhao, Y., Chen, S., Bu, Y., Zhu, X., Du, Y., Li, F. 2016. “A highly sensitive and selective colorimetric “Off-On” chemosensor for Cu2+ in aqueous media based on a rhodamine derivative bearing thiophene group”. Sensors and Actuators B: Chemical, 23, 414-419.
  • Yoon, J. W., Chang, M. J., Hong, S., Lee, M. H. 2017. “A fluorescent probe for copper and hypochlorite based on rhodamine hydrazide framework”. Tetrahedron Letter, 58, 3887-3893.
  • Yu, C., Wang, T., Xu, K., Zhao, J., Li, M., Weng, S., Zhang, J. 2013. “Characterization of a highly Cu2+-selective fluorescent probe derived from rhodamine B”. Dyes and Pigments, 96, 38-44.
  • Yu, C., Zhang, J., Li, J., Liu, P., Wei, P., Chen, L. 2011. “Fluorescent probe for copper (II) ion based on a rhodamine spirolactame derivative, and its application to fluorescent imaging in living cells”. Microchimica Acta, 174, 247-255.
  • Zhang, X., Shiraishi, Y., Hirai, T. 2007. “Cu (II)-selective green fluorescence of a rhodamine−diacetic acid conjugate”. Organic Letters, 9, 5039-5042.
  • Zhao, M., Yang, X. F., He, S., Wang, L. 2009. “A rhodamine-based chromogenic and fluorescent chemosensor for copper ion in aqueous media”. Sensors and Actuators B: Chemical, 135, 625-631.
  • Zhou, Y., Wang, F., Kim, Y., Kim, S. J., Yoon, J. 2009. “Cu2+-selective ratiometric and “off-on” sensor based on the rhodamine derivative bearing pyrene group”. Organic letters, 11, 4442-4445.
  • Zhou, Y., Zhang, J., Zhou, H., Zhang, Q., Ma, T., Niu, J. 2012. “A new rhodamine B-based “off–on” fluorescent chemosensor for Cu2+ in aqueous media”. Journal of Luminescence, 132, 1837-1841.

An Effective ‘Off-On’ Artificial Probe Based on Rhodamine B Derivative for Sensitive and Selective Recognition of Cu2+ Ions

Yıl 2020, Cilt: 13 Sayı: 2, 811 - 827, 31.08.2020
https://doi.org/10.18185/erzifbed.735011

Öz

This paper describes the synthesis and optical application of a novel, xanthane-based colorimetric and fluorescent `on-off’ sensor RhCHN for the selective recognition and discrimination of Cu2+ ions. Its structural characterization was achieved by NMR (1H and 13C), FT-IR sand LC-MS/MS analyses. Of the meatal ions tested, only addition of Cu2+ ions to the probe in buffer solution, the maximum increases in both absorption and fluorescent emission spectra at 565 and 588 nm, respectively, were observed, followed by an immediate change in color from colorless to purple, visible to the naked eye. It was found that the RhCHN probe showed remarkable selectivity and sensitivity to copper ions only among the metal ions initially used. According to Job's plot method, it was estimated that RhCHN is bound to the Cu2+ ion to form a complex within a 1:1 coordination stoichiometry (RhCHN:Cu2+). As stated in previous reports, a strong bond interaction between Cu2+ and RhCHN has most likely gone through the spirolactam ring opening process. With an acceptable detection limit for copper ions, the analytical applications implied that the chromogenic and fluorogenic double response probe RhCHN can be effectively used for direct visualization and detection of Cu2+ in aqueous medium.

Kaynakça

  • Adhikari, S., Ta, S., Ghosh, A., Guria, S., Pal, A., Ahir, M., Das, D. 2019. “A 1, 8 naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ ion in living cells”. Journal of Photochemistry and Photobiology A: Chemistry, 372, 49-58.
  • Chatterjee, N., Mahaling, B., Sivakumar, S., Bharadwaj, P. K. 2016. “A highly selective and sensitive “turn-on” fluorescence chemosensor for the Cu2+ ion in aqueous ethanolic medium and its application in live cell imaging”. Journal of Photochemistry and Photobiology A: Chemistry, 330 (2016), 110-116.
  • Dai, K., Xu, B., Chen, J. 2014. “A Rhodamine-based “off-on” colorimetric and fluorescent chemosensor for Cu (II) in aqueous and non-aqueous media”. Journal of Fluorescence, 24, 1129-1136.
  • Ding, H., Li, B., Pu, S., Liu, G., Jia, D., Zhou, Y. 2017. “A fluorescent sensor based on a diarylethene-rhodamine derivative for sequentially detecting Cu2+ and arginine and its application in keypad lock”. Sensors and Actuators B: Chemical, 247, 26-35.
  • Ding, J., Yuan, L., Gao, L., Chen, J. 2012. “Fluorescence quenching of a rhodamine derivative: selectively sensing Cu2+ in acidic aqueous media”. Journal of Luminescence, 132, 1987-1993.
  • Dong, M., Ma, T. H., Zhang, A. J., Dong, Y. M., Wang, Y. W., Peng, Y. 2010. “A series of highly sensitive and selective fluorescent and colorimetric “off-on” chemosensors for Cu (II) based on rhodamine derivatives”. Dyes and pigments, 87, 164-172.
  • Franco, L. L., Almeida, M. V. de, Silva, L. F. R. e, Vieira, P. P. R., Pohlit, A. M., Valle, M. S. 2012. “Synthesis and antimalarial activity of dihydroperoxides and tetraoxanes conjugated with bis (benzyl) acetone derivatives”. Chemical biology & drug design, 79, 790-797.
  • Guo, D., Dong, Z., Luo, C., Zan, W., Yan, S., Yao, X. 2014. “A rhodamine B-based “turn-on” fluorescent sensor for detecting Cu 2+ and sulfur anions in aqueous media”. RSC Advances, 4(11), 5718-5725.
  • Hu, J. H., Long, C., Fu, Q. Q., Ni, P. W., Yin., Z. Y. 2019. “A novel highly selective colorimetric and “turn-on” fluorimetric chemosensor for detecting Hg2+ based on Rhodamine B hydrazide derivatives in aqueous media”. Journal of Photochemistry and Photobiology A: Chemistry, 379, 105-111.
  • Hu, Y., Zhang, J., Lv, Y. Z., Huang, X. H., Hu, S. L. 2016. “A new rhodamine-based colorimetric chemosensor for naked-eye detection of Cu2+ in aqueous solution”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 157, 164-169.
  • Hu, Z. Q., Wang, X. M., Feng, Y. C., Ding, L., Lu, H. Y. 2011. “Sulfonyl rhodamine hydrazide: A sensitive and selective chromogenic and fluorescent chemodosimeter for copper ion in aqueous media”. Dyes and Pigments, 88, 257-261.
  • Huo, F., Wang, L., Yin, C. , Yang, Y., Tong, H., Chao, J., Zhang, Y. 2013. “The synthesis, characterization of three isomers of rhodamine derivative and their application in copper (II) ion recognition”. Sensors and Actuators B: Chemical, 188, 735-740.
  • Jiang, Z., Tian, S., Wei, C., Ni, T., Li, Y., Dai, L., Zhang, D. 2013. “A novel selective and sensitive fluorescent turn-on chemodosimeter based on rhodamine hydrazone for copper ions and its application to bioimaging”. Sensors and Actuators B: Chemical, 184, 106-112.
  • Jiao, Y., Liu, X., Zhou, L., He, H., Zhou, P., Duan, C., Peng, X. 2018. “A fluorescein derivative-based fluorescent sensor for selective recognition of copper (II) ions”. Photochemistry and Photobiology A: Chemistry, 355, 67-71.
  • Jiao, Y., Zhou, L., He, H., Yin, J., Gao, Q., Wei, J., Duan, C., Peng, X. 2018. “A novel rhodamine B-based “off-on’’fluorescent sensor for selective recognition of copper (II) ions”. Talanta, 184, 143-148.
  • Kempahanumakkagaari, S. K., Thippeswamy, R., Malingappa, P. 2014. “A new rhodamine B based fluorometric chemodosimeter for Cu2+ ion in aqueous and cellular media”. Journal of Luminescence, 146, 11-17.
  • Li, G., Tao, F., Wang, H., Li, Y., Wang, L. 2015. “A novel reversible colorimetric chemosensor for rapid naked-eye detection of Cu2+ in pure aqueous solution”. Sensor and Actuators B: Chemical. 211, 325-331.
  • Li, K., Xiang, Y., Wang, X., Li, J., R. Hu, A., Tong, Tang, B. Z. 2014. “Reversible photochromic system based on rhodamine B salicylaldehyde hydrazone metal complex”. The Journal of the American Chemical Society, 136, 1643-1649.
  • Li, M., Lv, H. S., Luo, J. Z., Miao, J. Y., Zhao, B. X. 2013. “An effective “turn-on” rodamine-based fluorescent chemosensor for Cu (II) in living cells”. Sensors and Actuators B: Chemical, 188, 1235-1240.
  • Li, P., Zhou, H., Tang, B. 2012. “A lysosomal-targeted fluorescent probe for detecting Cu2+”. Journal of Photochemistry and Photobiology A: Chemistry, 249, 36-40.
  • Li, W., Zhang, Y., Gan, X., Yang, M., Mie, B., Fang, M., Zhang, Q., Yu, J., Wu, J., Tian, Y., Zhou, H. 2015. “A triphenylamine-isophorone-based “off–on” fluorescent and colorimetric probe for Cu2+”. Sensors and Actuators B: Chemical, 206, 640-646.
  • Lou, X., Qiang, L., Qin, J., Li, Z. 2009. “A new rhodamine-based colorimetric cyanide chemosensor: convenient detecting procedure and high sensitivity and selectivity”. ACS Applied Materials & Interfaces, 1, 2529-2535.
  • Lv, L., Diao, Q. 2017. “A highly selective and sensitive rhodamine-derived fluorescent probe for detection of Cu2+”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 179, 221-226.
  • Lv, T., Xu, Y., Li, H., Liu, F., Sun, S. 2018. “A Rhodamine B-based fluorescent probe for imaging Cu2+ in maize roots”. Bioorganic & Medicinal Chemistry Letters, 26, 1448-1452.
  • Mergu, N., Gupta, V. K. 2015. “A novel colorimetric detection probe for copper (II) ions based on a Schiff base”. Sensor and Actuators B: Chemical, 210, 408-417.
  • Min, M., Wang, X., Chen, Y., Wang, L., Huang, H., Shi, J. 2013. “Highly sensitive and selective Cu2+ sensor based on electrospun rhodamine dye doped poly (ether sulfones) nanofibers”. Sensors and Actuators B: Chemical,188, 360-366.
  • Muthuraj, B., Deshmukh, R., Trivedi, V., Iyer, P. K. 2014. “Highly selective probe detects Cu2+ and endogenous no gas in living cell”. ACS Applied Materials & Interfaces, 6, 6562-6569.
  • Nair, R. Raju, R., M., Patel, N. P., Raval, I. H., Suresh, E., Haldar, S., Chatterjee, P. B. 2015. “Naked eye instant reversible sensing of Cu2+ and its in situ imaging in live brine shrimp, artemia”. Analyst. 140, 5464-5468.
  • Ozdemir, M. 2017. “A fast-response, highly selective, chromogenic and fluorescent chemosensor for the detection of Hg2+ ions”. Sensors and Actuators B: Chemical, 249, 217-228.
  • Ozdemir, M. 2019. “A novel chromogenic molecular sensing platform for highly sensitive and selective detection of Cu2+ ions in aqueous environment”. Journal of Photochemistry and Photobiology A: Chemistry, 369, 54-69.
  • Ozdemir, M. 2016. “A rhodamine-based colorimetric and fluorescent probe for dual sensing of Cu2+ and Hg2+ ions”. Journal of Photochemistry and Photobiology A: Chemistry, 318, 7-13, 2016.
  • Puangploy, P., Smanmoo, S., Surareungchai, W. 2014. “A new rhodamine derivative-based chemosensor for highly selective and sensitive determination of Cu2+”. Sensors and Actuators B: Chemical, 193, 679-686
  • Reddy, N.S.K., Badam, R., Sattibabu, R., Molli, M., Muthukumar, V.S., Sai, S.S.S., Rao, G.N. 2014. “Synthesis, characterization and nonlinear optical properties of symmetrically substituted dibenzylideneacetone derivatives”. Chemical Physics Letters, 616 (2014), 142-147.
  • Sahana, S., Mishra, G., Sivakumar, S., Bharadwaj, P. K. 2017. “Highly sensitive and selective “turn-on” chemodosimeter based on Cu2+-promoted hydrolysis for nanomolar detection of Cu2+ and its application in confocal cell imaging”. Journal of Photochemistry and Photobiology A: Chemistry, 334, 47-54.
  • Saleem, M., Lee, K. H. 2014. “Selective fluorescence detection of Cu2+ in aqueous solution and living cells”. Journal of Luminescence, 145, 843-848.
  • Sun, T., Li, Y., Niu, Q., Li, T., Liu, Y. 2018. “Highly selective and sensitive determination of Cu2+ in drink and water samples based on a 1, 8-diaminonaphthalene derived fluorescent sensor”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 198, 142-147.
  • Sun, Z., Li, H., Guo, D., Liu, Y., Tian, Z., Yan, S. 2015. “A novel piperazine-bis (rhodamine-B)-based chemosensor for highly sensitive and selective naked-eye detection of Cu2+ and its application as an INHIBIT logic device”. Journal of Luminescence, 167, 156-162.
  • Tang, L., Guo, J., Wang, N. 2013. “A New Rhodamine B Hydrazide Hydrazone Derivative for Colorimetric and Fluorescent”. Bulletin of the Korean Chemical Society, 34, 159-163.
  • Tang, R., Lei, K., Chen, K., Zhao, H., Chen, J. 2011. “A rhodamine-based off–on fluorescent chemosensor for selectively sensing Cu (II) in aqueous solution”. Journal of Fluorescence, 21, 141-148.
  • Tang, X., Zhu, Z., Wang, Y., Han, J., Ni, L., Wang, L., Zhang, H., Li, J., Qiu, Y. 2018. “A dual site controlled probe for fluorescent monitoring of intracellular pH and colorimetric monitoring of Cu2+”. Sensors and Actuators B: Chemical, 270, 35-44.
  • Udhayakumari, D., Naha, S., Velmathi, S. 2017. “Colorimetric and fluorescent chemosensors for Cu 2+, A comprehensive review from the years 2013–15”. Analytical Methods, 9, 552-578.
  • Wang, J., Li, H., Long, L., Xiao, G., Xie, D. 2012. “Fast responsive fluorescence turn-on sensor for Cu2+ and its application in live cell imaging”. Journal of Lumines cence,132, 2456-2461.
  • Wang, J., Long, L., Xie, D., Song, X. 2013. “Cu2+-selective “Off–On” chemsensor based on the rhodamine derivative bearing 8-hydroxyquinoline moiety and its application in live cell imaging”. Sensors and Actuators B: Chemical, 17, 27-33.
  • Wang, M., Yan, F., Zou, Y., Chen, L., Yang, N., Zhou, X. 2014. “Recognition of Cu2+ and Hg2+ in physiological conditions by a new rhodamine based dual channel fluorescent probe”. Sensor and Actuators B: Chemical, 192, 512-521.
  • Wang, R., Ren, P., Pu, S., Liu, G., Cui, S. 2014. “Novel sensitive sensors for Cu2+ and optical switching of photochromic dithienylethene derivatives”. Journal of Photochemistry and Photobiology A: Chemistry, 294, 44-53.
  • Wang, X., Tao, J., Chen, X., Yang, H. 2017. “An ultrasensitive and selective “off-on” rhodamine-based colorimetric and fluorescent chemodosimeter for the detection of Cu2+”. Sensors and Actuators B: Chemical, 244, 709-716.
  • Wang, Y., Chang, H. Q., Wu, W. N., Mao, X. J., Zhao, X. L., Yang, Y., Jia, L. 2017. “A highly sensitive and selective colorimetric and off–on fluorescent chemosensor for Cu2+ based on rhodamine 6G hydrazide bearing thiosemicarbazide moiety”. Journal of Photochemistry and Photobiology A: Chemistry, 335, 10-16.
  • Wang, Y., Wu, H. Q., Sun, J. H., Liu, X. Y., Luo, J., Chen, M. Q. 2012. “A novel chemosensor based on rhodamine derivative for colorimetric and fluorometric detection of Cu2+ in aqueous solution”. Journal of Fluorescence, 22, 799-805.
  • Wu, S. P., Huang, Z. M., Liu, S. R., Chung, P. K. 2012. “A pyrene-based highly selective turn-on fluorescent sensor for copper (II) ion and its application in live cell imaging”. Journal of Fluorescence, 22, 253-259.
  • Xiang, Y., Tong, A., Jin, P., Ju, Y. 2006. “New fluorescent rhodamine hydrazone chemosensor for Cu (II) with high selectivity and sensitivity”. Organic letters, 8, 2863-2866.
  • Xu, J., Hou, Y., Ma, Q., Wu, X., Feng, S., Zhang, J., Shen, Y. 2014. “A highly selective fluorescent probe for Cu2+ based on rhodamine B derivative”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 124, 416-422.
  • Xu, L., Wei, S., Diao, Q., Ma, P., Liu, X., Sun, Y., Song, D., Wang, X. 2017. “Sensitive and selective rhodamine-derived probes for fluorometric sensing of pH and colorimetric sensing of Cu2+”. Sensors and Actuators B: Chemical, 246, 395-401.
  • Xu, Z., Zhang, L., Guo, R., Xiang, T., Wu, C., Zheng, Z., Yang, F. 2011. “A highly sensitive and selective colorimetric and off–on fluorescent chemosensor for Cu 2+ based on rhodamine B derivative”. Sensors and Actuators B: Chemical, 156, 546-552.
  • Yang, Z., Zhao, Y., Chen, S., Bu, Y., Zhu, X., Du, Y., Li, F. 2016. “A highly sensitive and selective colorimetric “Off-On” chemosensor for Cu2+ in aqueous media based on a rhodamine derivative bearing thiophene group”. Sensors and Actuators B: Chemical, 23, 414-419.
  • Yoon, J. W., Chang, M. J., Hong, S., Lee, M. H. 2017. “A fluorescent probe for copper and hypochlorite based on rhodamine hydrazide framework”. Tetrahedron Letter, 58, 3887-3893.
  • Yu, C., Wang, T., Xu, K., Zhao, J., Li, M., Weng, S., Zhang, J. 2013. “Characterization of a highly Cu2+-selective fluorescent probe derived from rhodamine B”. Dyes and Pigments, 96, 38-44.
  • Yu, C., Zhang, J., Li, J., Liu, P., Wei, P., Chen, L. 2011. “Fluorescent probe for copper (II) ion based on a rhodamine spirolactame derivative, and its application to fluorescent imaging in living cells”. Microchimica Acta, 174, 247-255.
  • Zhang, X., Shiraishi, Y., Hirai, T. 2007. “Cu (II)-selective green fluorescence of a rhodamine−diacetic acid conjugate”. Organic Letters, 9, 5039-5042.
  • Zhao, M., Yang, X. F., He, S., Wang, L. 2009. “A rhodamine-based chromogenic and fluorescent chemosensor for copper ion in aqueous media”. Sensors and Actuators B: Chemical, 135, 625-631.
  • Zhou, Y., Wang, F., Kim, Y., Kim, S. J., Yoon, J. 2009. “Cu2+-selective ratiometric and “off-on” sensor based on the rhodamine derivative bearing pyrene group”. Organic letters, 11, 4442-4445.
  • Zhou, Y., Zhang, J., Zhou, H., Zhang, Q., Ma, T., Niu, J. 2012. “A new rhodamine B-based “off–on” fluorescent chemosensor for Cu2+ in aqueous media”. Journal of Luminescence, 132, 1837-1841.
Toplam 61 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Mecit Özdemir 0000-0003-4763-0360

Yusuf Yılmaz 0000-0003-4363-0427

Yayımlanma Tarihi 31 Ağustos 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 13 Sayı: 2

Kaynak Göster

APA Özdemir, M., & Yılmaz, Y. (2020). An Effective ‘Off-On’ Artificial Probe Based on Rhodamine B Derivative for Sensitive and Selective Recognition of Cu2+ Ions. Erzincan University Journal of Science and Technology, 13(2), 811-827. https://doi.org/10.18185/erzifbed.735011