3, 3,5 and 2,6 Expanded Aza-BODIPYs Via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: Synthesis and Photo
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ORIGINAL ARTICLE
3, 3,5 and 2,6 Expanded Aza-BODIPYs Via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions: Synthesis and Photophysical Properties Halil Yılmaz 1
&
Gökhan Sevinç 2
&
Mustafa Hayvalı 1
Received: 9 September 2020 / Accepted: 30 October 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Novel symmetrical aza-borondipyrromethene (aza-BODIPY) compounds bearing 4-methoxyphenyl, 4-methoxybiphenyl, 2,4dimethoxybipheny, 4-bromophenyl and N,N-diphenyl-4-biphenylamine groups on the 3, 3,5 and 2,6 positions of aza-BODIPY core were synthesized via Suzuki-Miyaura coupling reactions while unsymmetrical analogues were obtained from the starting mono Br-substituted aza-BODIPY material which was obtained from nitrosolated pyrrole derivative. The characterizations were performed by means of 1H-NMR, 13C-NMR, FTIR and HRMS-TOF-ESI techniques. The spectral properties of the aza-BODIPY derivatives were investigated using absorption and fluorescence spectroscopy. The novel compounds with extended conjugation have broadband absorption in near infrared region and show significant shifts on their absorption and fluorescence spectra compared to unsubstituted analogues. The highest bathochromic shifts were observed π-extended and strong electron donating groups at 3,5 positions of the aza-BODIPY scaffold. Depend on substitution positions of attached groups to the indacene core, the fluorescence quantum yields of chromophores were determined to be drastic changes. The singlet oxygen generation capability of the compounds were evaluated and 2,6-bromine substituted compounds AA1 and CC1 showed high singlet oxygen quantum yields (71% and 74%, respectively). Enhanced photophysical properties such as intense absorption, extended conjugation and singlet oxygen production make the investigated aza-BODIPYs promising candidates for photodynamic therapy applications and organic photovoltaic cells in NIR region. Keywords Aza-BODIPY . Unsymmetrical aza-BODIPY . Azadipyrromethenes . Suzuki-Miyaura coupling . NIR region dyes
Introduction Although, the first reaction of tetraarylazadipyrromethenes with boron (Aza-BODIPY) occurred in the early 1990s [1] these dyes have been recognized by the studies of the O’Shea group since 2002 [2].Aza-BODIPY dyes are azaanalogous of difluorobora-diaza-s-indacenes (BODIPY) and known as attractive fluorophores because of their Supplementary Information The online version contains supplementary material available at https://doi.org/10.1007/s10895-02002646-4. * Mustafa Hayvalı [email protected] 1
Department of Chemistry, Faculty of Science, Ankara University, Anadolu, 06100 Ankara, Turkey
2
Department of Chemistry, Faculty of Science and Literature, Bilecik Şeyh Edebali University, 11230 Bilecik, Turkey
advantageous features. Sharp absorption and fluorescence bands, large molar extinction coefficients, high fluorescence quantum yields and high photostability [3–5] all contribute to the appeal of these interesting compounds. Aza-BODIPY comp
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