Friday, 8 November 2024 11:00am – 12:00pm

This seminar will be delivered in Lecture Theatre 2

Speaker: Professor Daniel Werz

Host: Dr Constance Bailey

Title: Design and Serendipity in Fluorophore Chemistry

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.

Scheme 1: BODIPY, (Aza-)BOIMPY and highly conjugated BODIPY oligomer.

[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.

Bio
Daniel B. Werz studied chemistry at the University of Heidelberg (Germany) and University of Bristol (UK) supported by the German National Merit Foundation. After finishing his PhD thesis on electron-rich alkynes in 2003 he started postdoctoral work with Peter H. Seeberger at ETH Zurich (Switzerland). After his habilitation in 2011 at Göttingen University he became Associate and Full Professor in Braunschweig. In 2022 he moved to his present position as Full Professor and Chair of Organic Chemistry at the University of Freiburg (Germany). He has been a visiting professor in Kyoto (Japan), in Tel Aviv (Israel), in Mumbai and in Guwahati (India). His research interests ranging from strained ring systems, to cascade reactions, carbohydrate and fluorophore chemistry were documented in more than 250 publications.