Synthesis and Properties of Carboxylic Acid Functionalized Near IR Absorbing Thiophene Fused BODIPY Compounds
Öz
Boron dipyrromethene dyes are one of the most important types of compounds in various fields such as chemical indicators, biological labelling, photodynamic therapy, and solar cells. One of the important derivatives of these dyes are the thiophene-fused BODIPY structures. These structures impart special features such as near IR absorption, heavy atom free photosensitization and compact structure. Although having important aspects, these derivatives of dyes suffer from low synthetic yields. In a few decades various derivatives of fused BODIPY structures were published. However, still more studies are needed to increase the number of these dyes in order to exploit more features and increase the synthetic yields. In the current work, two near-infrared absorbing thiophene fused Bodipy compounds, named CTFBOD1-2, were designed, synthesized and characterized using various techniques. Both compounds were substituted with meso-4-carboxyphenyl units since we have investigated their potential for dye-sensitized solar cell structures. And as electron donor structures, 4-methoxyphenyl and hexylthiophene units were attached to form a donor-acceptor structure. Photophysical and cyclic voltammetry characterizations were also accomplished. In the hexyl-thiophene attached structure (CTFBOD2) we have observed more bathochromic shift in both absorption and emission probably due to the stronger electron pull ability of the thiophene unit. With this structure up to 775 nm absorption is observed, and it is highly important to reach this window with compact structures for solar harvesting. We have observed that the compounds could have been investigated as building blocks in various fields such as dye-sensitized solar cell concept as a photosensitizer.
Anahtar Kelimeler
BODIPY, Chemosensors, Dyes, Dye sensitized solar cell, Photodynamic therapy
Destekleyen Kurum
The author thanks TUBITAK (Project No: 216Z015) for financial support
Proje Numarası
216Z015
Kaynakça
- P. De Bonfils, L. Péault, P. Nun, V. Coeffard, State of the art of bodipy-based photocatalysts in organic synthesis, European Journal of Organic Chemistry. 12 (2021), 1809-1824.
- N. Boens, B. Verbelen, W. Dehaen, Postfunctionalization of the BODIPY core: synthesis and spectroscopy. European Journal of Organic Chemistry. 30 (2015), 6577-6595.
- Y. Cakmak, Synthesis and investigation of a hexyl substituted thieno-fused BODIPY derivative as a versatile near-IR fluorophore, Turkish Journal of Chemistry. 46 (2022), 1120-1127.
- M. Tok, B. Say, G. Dölek, B. Tatar, D. Özgur, Ç. Kurukavak, M. Kus, Y. Dede, Y. Çakmak, Substitution effects in distyryl BODIPYs for near infrared organic photovoltaics, Journal of Photochemistry and Photobiology A-Chemistry. 429 (2022), 113933.
- B. Can, Y. Çakmak, Exploration of Two Different Strategies in Near IR Absorbing Boron Dipyrromethene Derivatives for Photodynamic and Bioimaging Purposes, ChemistrySelect. 6 (2021), 8855-8860.
- O. Buyukcakir, O. Bozdemir, S. Kolemen, S. Erbas, E. Akkaya, Tetrastyryl-Bodipy dyes: Convenient synthesis and characterization of elusive Near IR fluorophores, Organic Letters. 11 (2009), 4644-4647.
- B. Kukrer, E. U. Akkaya, Red to near IR fluorescent signalling of carbohydrates, Tetrahedron Letters. 40 (1999), 9125-9128.
- T. Bura, N. Leclerc, S. Fall, P. Lévêque, T. Heiser, P. Retailleau, S. Rihn, A. Mirloup, R. Ziessel, High-performance solution-processed solar cells and ambipolar behavior in organic field-effect transistors with Thienyl-BODIPY Scaffoldings, Journal of the American Chemical Society. 134 (2012), 17404-17407.
- S. Kolemen, O. A. Bozdemir, Y. Cakmak, G. Barin, S. Erten-Ela, M. Marszalek, J. H. Yum, S. M. Zakeeruddin, M. K. Nazeeruddin, M. Gratzel and E. U. Akkaya, Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells, Chemical Science. 2 (2011), 949-954.
- S. Erten-Ela, M. Yilmaz, B. Icli, Y. Dede, S. Icli, E. U. Akkaya, A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells, Organic Letters. 10 (2008), 3299-3302.