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

被引：3

作者：

Roger, Maxime ^{[1
]}

Bretonniere, Yann ^{[2
]}

Trolez, Yann ^{[3
]}

Vacher, Antoine ^{[3
]}

Arbouch, Imane ^{[4
]}

Cornil, Jerome ^{[4
]}

Felix, Gautier ^{[1
]}

De Winter, Julien ^{[5
]}

Richeter, Sebastien ^{[1
]}

Clement, Sebastien ^{[1
]}

Gerbier, Philippe ^{[1
]}

机构：

[1] Univ Montpellier, CNRS, ICGM, ENSCM,UMR 5253, F-34293 Montpellier, France

[2] Univ Lyon, ENS Lyon, CNRS, Lab Chim,UMR 5182, F-69364 Lyon, France

[3] Univ Rennes, Ecole Natl Super Chim Rennes, CNRS, ISCR,UMR 6226, F-35065 Rennes, France

[4] Univ Mons UMONS, Lab Chem Novel Mat, B-7000 Mons, Belgium

[5] Univ Mons UMONS, Organ Synth & Mass Spectrometry Lab S2MOs, B-7000 Mons, Belgium

来源：

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES | 2023年 / 24卷 / 10期

关键词：

TPE; AIEgen; cycloaddition-retroelectrocyclization; click chemistry; photothermal applications; AGGREGATION-INDUCED EMISSION; NONLINEAR-OPTICAL PROPERTIES; CHARGE-TRANSFER INTERACTIONS; DENSITY-FUNCTIONAL THEORY; ENERGY-LEVEL MODULATION; HOMO-LUMO GAP; PORPHYRIN DERIVATIVES; HIGHLY EFFICIENT; ORGANIC ALKYNES; CHEMISTRY;

D O I：

10.3390/ijms24108715

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 (F-4-TCNQ) as electron-deficient alkenes. Only the starting TPE-alkyne displayed significant AIE behavior, whereas for TPE-TCNE, a faint effect was observed, and for TPE-TCNQ and TPE-F-4-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-F-4-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 F-4-TCNQ with donor-substituted are promising candidates for PT applications.

引用

页数：22

共 121 条

[81] C3-Symmetric star shaped donor-acceptor truxenes: synthesis and photophysical, electrochemical and computational studies [J].