Synthesis and Theoretical Calculation of p-Aminostyryl-BODIPY Derivative: Trans-Configuration Selectivity of Knoevenagel Condensation Reaction
Abstract
BODIPY derivatives have become important
molecules because of their spectroscopic and biological properties and they
have been found some application fields such as florescent sensors,
photosensitizer and cellular imaging. To increase the competence of these
fields of BODIPYs, an extension of the conjugation is needed. For this purpose,
Knoevenagel condensation reaction
is generally performed. During this research, the synthesis of BODIPY 10 was achieved by performing Knoevenagel
condensation reaction and resulted in the formation of trans-configurated styryl-product. In addition to the synthetic
performance, we also examine the fate of the stereoselectivity by DFT
calculations.
Supporting Institution
Giresun Üniversitesi
Project Number
FEN-BAP-A-150219-25
Thanks
We are gratefully thankful to Prof. Dr. Engin U. AKKAYA for valuable support during this research and Giresun University for the financial support (Project Number: FEN-BAP-A-150219-25)
References
- Ekmekci, Z., Yilmaz, M. D., & Akkaya, E. U. (2008). A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. Organic Letters, 10(3), 461–464. https://doi.org/10.1021/ol702823u
- Knoevenagel, E. (1898). Condensation von Malonsäure mit aromatischen Aldehyd-en durch Ammoniak und Amine. Berichte Der Deutschen Chemischen Gesellschaft, 31(3), 2596–2619. https://doi.org/10.1002/cber.18980310308
- Kolemen, S., Bozdemir, O. A., Cakmak, Y., Barin, G., Erten-Ela, S., Marszalek, M., … Akkaya, E. U. (2011). Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells. Chemical Science, 2(5), 949–954. https://doi.org/-10.1039/C0SC00649A
- Kolemen, S., Cakmak, Y., Ozdemir, T., Erten-Ela, S., Buyuktemiz, M., Dede, Y., & Akkaya, E. U. (2014). Design and characterization of Bodipy derivatives for bulk heterojunction solar cells. Tetrahedron, 70(36), 6229–6234. https://doi.org/10.1016/j.tet.2014.03.049
- Kostereli, Z., Ozdemir, T., Buyukcakir, O., & Akkaya, E. U. (2012). Tetrastyryl-BODIPY-based dendritic light harvester and estimation of energy transfer efficiency. Organic Letters, 14(14), 3636–3639.
- Loudet, A., & Burgess, K. (2007). BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties. Chemical Reviews, 107(11), 4891–4932. https://doi.org/doi:10.1021/cr078381n
- Sozmen, F., Kolemen, S., Kumada, H.-O., Ono, M., Saji, H., & Akkaya, E. U. (2014). Designing BODIPY-based probes for fluorescence imaging of β-amyloid plaques. RSC Adv., 4(92), 51032–51037. https://doi.org/10.1039/C4RA07754G
- Wang, D., Shiraishi, Y., & Hirai, T. (2010). A distyryl BODIPY derivative as a fluorescent probe for selective detection of chromium(III). Tetrahedron Letters, 51(18), 2545–2549. https://doi.org/-10.1016/j.tetlet.2010.03.013
p-Aminostiril-BODIPY Türevinin Sentezi ve Teorik Hesaplamalarının Yapılması: Knoevenagel Kondenzasyon Reaksiyonunun trans-Konfigürasyon Seçiciliği
Abstract
BODIPY türevi malzemeler göstermiş
oldukları biyolojik ve spektroskopik özellikleri açısından önemli moleküller
haline gelmiş ve fluoresans sensör, fotoduyarlaştırıcı ve hücre görüntüleme
gibi bazı uygulama alanları bulmuşlardır. BODIPY türevlerinin göstermiş olduğu
bu özelliklerin yetkinliğini artırmak için yapı üzerindeki konjugasyonun
artırılması önem arz etmektedir. Bu amaçla uygulanan en yaygın yöntem Knoevenagel
kondenzasyon reaksiyonudur. Bu çalışma çerçevesinde, BODIPY 10 molekülünün sentezi Knoevenagel
kondenzasyon reaksiyonu ile gerçekleştirilmiş ve trans-konfigurasyona sahip ürün elde edilmiştir. Yapılan bu
sentetik çalışmaya ilaveten elde edilen trans-seçiciliğin
kaynağını anlama adına DFT hesaplamaları yapılmıştır.
Project Number
FEN-BAP-A-150219-25
References
- Ekmekci, Z., Yilmaz, M. D., & Akkaya, E. U. (2008). A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. Organic Letters, 10(3), 461–464. https://doi.org/10.1021/ol702823u
- Knoevenagel, E. (1898). Condensation von Malonsäure mit aromatischen Aldehyd-en durch Ammoniak und Amine. Berichte Der Deutschen Chemischen Gesellschaft, 31(3), 2596–2619. https://doi.org/10.1002/cber.18980310308
- Kolemen, S., Bozdemir, O. A., Cakmak, Y., Barin, G., Erten-Ela, S., Marszalek, M., … Akkaya, E. U. (2011). Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells. Chemical Science, 2(5), 949–954. https://doi.org/-10.1039/C0SC00649A
- Kolemen, S., Cakmak, Y., Ozdemir, T., Erten-Ela, S., Buyuktemiz, M., Dede, Y., & Akkaya, E. U. (2014). Design and characterization of Bodipy derivatives for bulk heterojunction solar cells. Tetrahedron, 70(36), 6229–6234. https://doi.org/10.1016/j.tet.2014.03.049
- Kostereli, Z., Ozdemir, T., Buyukcakir, O., & Akkaya, E. U. (2012). Tetrastyryl-BODIPY-based dendritic light harvester and estimation of energy transfer efficiency. Organic Letters, 14(14), 3636–3639.
- Loudet, A., & Burgess, K. (2007). BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties. Chemical Reviews, 107(11), 4891–4932. https://doi.org/doi:10.1021/cr078381n
- Sozmen, F., Kolemen, S., Kumada, H.-O., Ono, M., Saji, H., & Akkaya, E. U. (2014). Designing BODIPY-based probes for fluorescence imaging of β-amyloid plaques. RSC Adv., 4(92), 51032–51037. https://doi.org/10.1039/C4RA07754G
- Wang, D., Shiraishi, Y., & Hirai, T. (2010). A distyryl BODIPY derivative as a fluorescent probe for selective detection of chromium(III). Tetrahedron Letters, 51(18), 2545–2549. https://doi.org/-10.1016/j.tetlet.2010.03.013
Details
| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Makaleler |
| Authors | |
| Project Number | FEN-BAP-A-150219-25 |
| Publication Date | March 20, 2020 |
| Published in Issue | Year 2020 |