2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi

Yıl 2023, Cilt: 49 Sayı: 2, 37 - 45, 30.10.2023

Ersin Güler , Çağla Dursun Anaçoğlu

https://doi.org/10.35238/sufefd.1296205

Öz

Bu çalışmada 2,4-dimetil pirol kullanılarak iki adet Bodipy bileşiği hazırlanmıştır. Sentezlenen ara ürünler ve hedef bileşiklerin saf bir şekilde elde edilebilmesi için sentezin her aşamasında kolon kromatografisinden faydalanılmıştır. Elde edilen saf ürünler çeşitli metotlar ile karakterize edilmiştir. lk olarak erime noktası tayini yapılmış ve FT-IR spektrumları toplanmıştır. FT-IR spektroskopisi ile fonksiyonel grup analizleri yapıldıktan sonra, bileşiklerin dötöro-kloroform içerisinde 1H-NMR ve 13C-NMR spektrumları alınmıştır. Elde edilen bileşiklere B-Cl ve B1, olarak kısa isimler ile verilmiştir. Karakterizasyon işlemlerinden sonra bileşiklerinin spektroskopik özellikleri, floresans spektroskopisi ve UV-vis spektroskopisi ile incelenmiştir. Ayrıca hazırlanan bileşiklerin floresans özelliklerine çözücünün etkisi de araştırılmıştır.

Anahtar Kelimeler

Bodipy, floresan, 2-4 dimetil pirol, Spektroskopik özellikler

Destekleyen Kurum

Selcuk Üniversitesi BAP

Proje Numarası

20211019

Synthesis and investigation of spectroscopic properties of bodipy derivatives prepared with 2,4-dimethylpyrrole

Öz

In this study, two Bodipy compounds were prepared using 2,4-dimethyl pyrrole. Column chromatography was used at every stage of the synthesis in order to obtain the synthesized intermediates and target compounds in a pure form. The pure products obtained were characterized by various methods. First, melting point determination was made and FT-IR spectra were collected. After functional group analysis with FT-IR spectroscopy, 1H-NMR and 13C-NMR spectra of the compounds were taken in deutero-chloroform. The obtained compounds are given short names as B-Cl and B1. After the characterization processes, the spectroscopic properties of the compounds were investigated by fluorescence spectroscopy and UV-vis spectroscopy. In addition, the effect of the solvent on the fluorescence properties of the prepared compounds was investigated.

Anahtar Kelimeler

Bodipy, Fluorescence, 2-4 dimethyl pyrrole, Spectroscopic Properties

Proje Numarası

20211019

Kaynakça

• Arroyo, I. J., Hu, R., Merino, G., Tang, B. Z. ve Pena-Cabrera, E., 2009, The smallest and one of the brightest. Efficient preparation and optical description of the parent borondipyrromethene system, The Journal of organic chemistry, 74 (15), 5719-5722.
• Baslak, C. ve Kursunlu, A. N., 2018, A naked-eye fluorescent sensor for copper (II) ions based on a naphthalene conjugate Bodipy dye, Photochemical & Photobiological Sciences, 17, 1091-1097.
• Deng, M., Gong, D., Han, S.-C., Zhu, X., Iqbal, A., Liu, W., Qin, W. ve Guo, H., 2017, BODIPY based phenylthiourea derivatives as highly selective MeHg+ and Hg2+ ions fluorescent chemodosimeter and its application to bioimaging, Sensors and Actuators B: Chemical, 243, 195-202.
• Groves, B. R., Crawford, S. M., Lundrigan, T., Matta, C. F., Sowlati-Hashjin, S. ve Thompson, A., 2013, Synthesis and characterisation of the unsubstituted dipyrrin and 4, 4-dichloro-4-bora-3a, 4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework, Chemical communications, 49 (8), 816-818.
• Hinkeldey, B., Schmitt, A. ve Jung, G., 2008, Comparative photostability studies of BODIPY and fluorescein dyes by using fluorescence correlation spectroscopy, ChemPhysChem, 9 (14), 2019-2027.
• Kursunlu, A. N., Yilmaz, A. K., Yemisci, E. ve Guler, E., 2022, Photophysical challenges and antenna effect between click reaction-based Bodipy derivatives manufactured from Knorr pyrrole, Results in Chemistry, 4, 100460.
• Kursunlu, A. N., Sahin, E., Guler, E., 2016, Cu (II) chemosensor based on a fluorogenic bodipy-salophen combination: sensitivity and selectivity studies, Journal of fluorescence, 26, 1997-2004.
• Li, Q., Peng, M., Li, H., Zhong, C., Zhang, L., Cheng, X., Peng, X., Wang, Q., Qin, J. ve Li, Z., 2012, A new “turn-on” naphthalenedimide-based chemosensor for mercury ions with high selectivity: successful utilization of the mechanism of twisted intramolecular charge transfer, near-IR fluorescence, and cell images, Organic Letters, 14 (8), 2094-2097.
• Lin, Y.-C., 2010, Modified BODIPY probes to explore peroxisome function, Durham University.
• Liu, J., Liu, C. ve He, W., 2013, Fluorophores and their applications as molecular probes in living cells, Current Organic Chemistry, 17 (6), 564-579.
• Liu, Z., Zhang, C., Li, Y., Wu, Z., Qian, F., Yang, X., He, W., Gao, X. ve Guo, Z., 2009, A Zn2+ fluorescent sensor derived from 2-(pyridin-2-yl) benzoimidazole with ratiometric sensing potential, Organic Letters, 11 (4), 795-798.
• Loudet, A. ve Burgess, K., 2007, BODIPY dyes and their derivatives: syntheses and spectroscopic properties, Chemical reviews, 107 (11), 4891-4932.
• Ma, Y., Lai, G., Li, Z., Tan, W., Shen, Y. ve Wang, C., 2015, Two sensors based on π-extended TTF: synthesis and high selectivity for copper (II), Tetrahedron, 71 (46), 8717-8724.
• Oguz, M., Kursunlu, A. N. ve Yilmaz, M., 2020, Low-cost and environmentally sensitive fluorescent cellulose paper for naked-eye detection of Fe (III) in aqueous media, Dyes and Pigments, 173, 107974.
• Sevinç, G., 2013, Bordipirometen (BODIPY) BileĢiklerinin Sentezi ve Yapılarının Aydınlatılması, Yüksek lisans tezi, Ankara Üniversitesi, Fen Bilimleri Enstitüsü, Kimya ABD.
• Suzuki, Y. ve Yokoyama, K., 2015, Development of functional fluorescent molecular probes for the detection of biological substances, Biosensors, 5 (2), 337-363.
• Tram, K., Yan, H., Jenkins, H. A., Vassiliev, S. ve Bruce, D., 2009, The synthesis and crystal structure of unsubstituted 4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY), Dyes and Pigments, 82 (3), 392-395.
• Ulrich, G., Ziessel, R. ve Harriman, A., 2008, The chemistry of fluorescent bodipy dyes: versatility unsurpassed, Angewandte Chemie International Edition, 47 (7), 1184-1201.
• Wang, D., Shiraishi, Y. ve Hirai, T., 2010, A distyryl BODIPY derivative as a fluorescent probe for selective detection of chromium (III), Tetrahedron Letters, 51 (18), 2545-2549.
• Wang, L., Fang, G. ve Cao, D., 2015, A novel phenol-based BODIPY chemosensor for selective detection Fe3+ with colorimetric and fluorometric dual-mode, Sensors and Actuators B: Chemical, 207, 849-857.
• Wang, Y., Liu, Y., Miao, J., Ren, M., Guo, W. ve Lv, X., 2016, A novel Bodipy-based fluorescent probe for Au3+ ions with high selectivity and its application to bioimaging, Sensors and Actuators B: Chemical, 226, 364-369.
• Zhang, M., Hao, E., Xu, Y., Zhang, S., Zhu, H., Wang, Q., Yu, C. ve Jiao, L., 2012, One-pot efficient synthesis of pyrrolylBODIPY dyes from pyrrole and acyl chloride, RSC advances, 2 (30), 11215-11218.
• Zhu, M.-Q., Gu, Z., Zhang, R., Xiang, J.-N. ve Nie, S., 2010, A stilbene-based fluoroionophore for copper ion sensing in both reduced and oxidized environments, Talanta, 81 (1-2), 678-683.