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

Year 2023, , 37 - 45, 30.10.2023
https://doi.org/10.35238/sufefd.1296205

Abstract

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.

Supporting Institution

Selcuk Üniversitesi BAP

Project Number

20211019

References

  • 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.

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

Year 2023, , 37 - 45, 30.10.2023
https://doi.org/10.35238/sufefd.1296205

Abstract

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.

Project Number

20211019

References

  • 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.
There are 23 citations in total.

Details

Primary Language Turkish
Subjects Structural Biology, Environmental Sciences, Agricultural Engineering
Journal Section Research Articles
Authors

Ersin Güler 0000-0003-2239-6774

Çağla Dursun Anaçoğlu This is me 0000-0001-9552-7267

Project Number 20211019
Publication Date October 30, 2023
Submission Date May 12, 2023
Published in Issue Year 2023

Cite

APA Güler, E., & Dursun Anaçoğlu, Ç. (2023). 2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, 49(2), 37-45. https://doi.org/10.35238/sufefd.1296205
AMA Güler E, Dursun Anaçoğlu Ç. 2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi. sufefd. October 2023;49(2):37-45. doi:10.35238/sufefd.1296205
Chicago Güler, Ersin, and Çağla Dursun Anaçoğlu. “2,4-Dimetilpirol Ile hazırlanan Bodipy türevlerinin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49, no. 2 (October 2023): 37-45. https://doi.org/10.35238/sufefd.1296205.
EndNote Güler E, Dursun Anaçoğlu Ç (October 1, 2023) 2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49 2 37–45.
IEEE E. Güler and Ç. Dursun Anaçoğlu, “2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi”, sufefd, vol. 49, no. 2, pp. 37–45, 2023, doi: 10.35238/sufefd.1296205.
ISNAD Güler, Ersin - Dursun Anaçoğlu, Çağla. “2,4-Dimetilpirol Ile hazırlanan Bodipy türevlerinin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 49/2 (October 2023), 37-45. https://doi.org/10.35238/sufefd.1296205.
JAMA Güler E, Dursun Anaçoğlu Ç. 2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi. sufefd. 2023;49:37–45.
MLA Güler, Ersin and Çağla Dursun Anaçoğlu. “2,4-Dimetilpirol Ile hazırlanan Bodipy türevlerinin Sentezi Ve Spektroskopik özelliklerinin Incelenmesi”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, vol. 49, no. 2, 2023, pp. 37-45, doi:10.35238/sufefd.1296205.
Vancouver Güler E, Dursun Anaçoğlu Ç. 2,4-Dimetilpirol ile hazırlanan bodipy türevlerinin sentezi ve spektroskopik özelliklerinin incelenmesi. sufefd. 2023;49(2):37-45.

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