Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis and Characterization of Tetraphenylethene AIEgen-Based Push-Pull Chromophores for Photothermal Applications: Do the Cycloaddition – Retroelectrocyclization Click Reaction Could Make any Molecule Photothermally Active?

Maxime Roger
,
Yann Bretonnière
,
Yann Trolez
ORCID logo ,
Antoine Vacher
,
Imane Arbouch
ORCID logo ,
Jérôme Cornil
,
Gautier Félix
ORCID logo ,
Julien De Winter
ORCID logo ,
Sébastien Richeter
,
Sébastien Clément
* ORCID logo ,
Philippe Gerbier
* ORCID logo
Version 1 : Received: 14 April 2023 / Approved: 17 April 2023 / Online: 17 April 2023 (04:02:21 CEST)

A peer-reviewed article of this Preprint also exists.

Roger, M.; Bretonnière, Y.; Trolez, Y.; Vacher, A.; Arbouch, I.; Cornil, J.; Félix, G.; Winter, J.D.; Richeter, S.; Clément, S.; Gerbier, P. Synthesis and Characterization of Tetraphenylethene AIEgen-Based Push–Pull Chromophores for Photothermal Applications: Could the Cycloaddition–Retroelectrocyclization Click Reaction Make any Molecule Photothermally Active? Int. J. Mol. Sci. 2023, 24, 8715. Roger, M.; Bretonnière, Y.; Trolez, Y.; Vacher, A.; Arbouch, I.; Cornil, J.; Félix, G.; Winter, J.D.; Richeter, S.; Clément, S.; Gerbier, P. Synthesis and Characterization of Tetraphenylethene AIEgen-Based Push–Pull Chromophores for Photothermal Applications: Could the Cycloaddition–Retroelectrocyclization Click Reaction Make any Molecule Photothermally Active? Int. J. Mol. Sci. 2023, 24, 8715.

Abstract

Three new tetraphenylethene (TPE) push-pull chromophores exhibiting strong intramolecular charge transfer (ICT) are described. They were obtained via [2+2] cycloaddition - retroelectrocyclization (CA-RE) click reactions on an electron-rich alkyne-tetrafunctionalized TPE (TPE-alkyne) using both 1,1,2,2-tetracyanoethene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) as electron-deficient alkene. Only the starting TPE-alkyne displayed a significant AIE behavior, whereas for TPE-TCNE,a faint effect was observed and for TPE-TCNQ and TPE-F4-TCNQ, no fluorescence was observed in any conditions. The main ICT bands that dominate the UV-Visible absorption spectra underwent a pronounced red-shift beyond the near-infrared (NIR) region for TPE-F4-TCNQ. Based on TD-DFT calculations, it was shown that the ICT character shown by the compounds exclusively originated from the clicked moieties independently of the nature of the central molecular platform. Photothermal (PT) studies conducted on both TPE-TCNQ and TPE-F4-TCNQ in the solid state revealed excellent properties, especially for TPE-F4-TCNQ. These results indicated that CA-RE reaction of TCNQ or F4-TCNQ with donor-substituted are promising candidates for PT applications.

Keywords

TPE; AIEgen; cycloaddition-retroelectrocyclization; CA-RE; click chemistry; photothermal appli-cations

Subject

Chemistry and Materials Science, Electronic, Optical and Magnetic Materials

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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