Organic Chemistry Seminar: Design and Serendipity in Fluorophore Chemistry
Prof. Daniel B. Werz, Institute of Organic Chemistry, Albert-Ludwigs-Universität Freiburg, Germany
Abstract:
The rich chemistry of the BODIPY motif, together with its beneficial photophysical properties, has markedly boosted the popularity of this user-friendly fluorophore over the last few decades.[1] The diversity of easily incorporated fluorescence modulation modes has set the stage for a variety of sensorically active species.
The talk describes which physical-organic rationalisation led to the development of the BOIMPY motif showing a significant red-shift with respect to the parent BODIPY.[2] In addition, a simple synthetic route to oligomerized ethano-linked BODIPYs (up to an octamer) is presented which can be further oxidized to huge completely conjugated systems.[3] Photophysical properties and biological properties are discussed by experimental and theoretical means.[4] It is shown that the suprastructure of the oligomeric dyes plays a significant role for their absorption and emission properties and that the conjugated systems are interesting NIR fluorophores.
[1] a) A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891; b) G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. 2008, 47, 1184.
[2] a) L. J. Patalag, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2016, 55, 13340; b) L. J. Patalag, P. G. Jones, D. B. Werz, Chem. Eur. J. 2017, 23, 15903.
[3] a) L. J. Patalag, L. Phong Ho, P. G. Jones, D. B. Werz, J. Am. Chem. Soc. 2017, 139, 15104; b) A. Patra, L. J. Patalag, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2021, 60, 747.
[4] L. J. Patalag, S. Ahadi, O. Lashchuk, P. G. Jones, S. Ebbinghaus, D. B. Werz, Angew. Chem. Int. Ed. 2021, 60, 8766-8771.
Event Organizer: Dr. Muhammad Jbara
