Modular functionalization and hydrogel formation via red-shifted and self-reporting [2+2] cycloadditions

Simon Ludwanowski; Daniel Hoenders; Kubra Kalayci; Hendrik Frisch; Christopher Barner-Kowollik; Andreas Walther

doi:10.1039/D0CC07429B

Modular functionalization and hydrogel formation via red-shifted and self-reporting [2+2] cycloadditions†

Simon Ludwanowski,

*^abcd Daniel Hoenders,^abcde Kubra Kalayci,^fg Hendrik Frisch,

^fg Christopher Barner-Kowollik

^fg and Andreas Walther

*^abcde

Author affiliations

* Corresponding authors

^a Institute for Macromolecular Chemistry, University of Freiburg, Stefan-Meier-Straße 31, 79104 Freiburg, Germany
E-mail: simon.ludwanowski@makro.uni-freiburg.de, andreas.walther@uni-mainz.de

^b Freiburg Materials Research Center (FMF), University of Freiburg, Stefan-Meier-Straße 21, 79104 Freiburg, Germany

^c Freiburg Center for Interactive Materials and Bioinspired Technologies (FIT), University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany

^d Cluster of Excellence livMatS @ FIT – Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, D-79110 Freiburg, Germany

^e A3BMS Lab, Department of Chemistry, University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany

^f Centre for Materials Science, Queensland University of Technology (QUT), 2 George Street, Brisbane, QLD 4000, Australia

^g School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George Street, Brisbane, QLD 4000, Australia

Abstract

We present a modularly applicable, red-shifted and self-reporting photodynamic covalent crosslinker, abbreviated qStyPy, that performs [2+2] cycloadditions upon irradiation with 470 nm in water. The rational design of qStyPy increases its hydrophilicity due to a permanent charge and features a broad emission in the far-red/near-infrared regime as a readout for the cycloadduct formation, rendering qStyPy suitable for biomedical applications.

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DOI: https://doi.org/10.1039/D0CC07429B
Article type: Communication
Submitted: 11 Nov 2020
Accepted: 16 Dec 2020
First published: 16 Dec 2020

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Chem. Commun., 2021,57, 805-808

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Modular functionalization and hydrogel formation via red-shifted and self-reporting [2+2] cycloadditions

S. Ludwanowski, D. Hoenders, K. Kalayci, H. Frisch, C. Barner-Kowollik and A. Walther, Chem. Commun., 2021, 57, 805 DOI: 10.1039/D0CC07429B

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Chemical Communications

Modular functionalization and hydrogel formation via red-shifted and self-reporting [2+2] cycloadditions†

Abstract

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Modular functionalization and hydrogel formation via red-shifted and self-reporting [2+2] cycloadditions

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