Bis(triarylmethylium)‐type Macrocyclic Dications: Mechanochromic Emission Extending to the Red Region

Macrocyclic dications 22+ composed of two triarylmethylium units were designed and synthesized. In contrast to the reference monocations 1+, macrocyclic dications 22+ exhibited mechanochromic emission extending to the red region (−900 nm), since the luminescence color in a solid state can reversibly...

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Published inChemPlusChem (Weinheim, Germany) Vol. 88; no. 3; pp. e202300110 - n/a
Main Authors Ishigaki, Yusuke, Tachibana, Takuya, Sugawara, Kazuma, Kikuchi, Moto, Suzuki, Takanori
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2023
Subjects
carbocations
Chemistry
Chemistry, Multidisciplinary
macrocycles
mechanochromism
Physical Sciences
red emission
Science & Technology
solid-state emission
DESIGN
DYES
LUMINESCENCE
FLUORESCENCE
macrocycles
AGGREGATION-INDUCED EMISSION
carbocations
mechanochromism
MECHANOFLUOROCHROMISM
solid-state emission
red emission
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Summary:Macrocyclic dications 22+ composed of two triarylmethylium units were designed and synthesized. In contrast to the reference monocations 1+, macrocyclic dications 22+ exhibited mechanochromic emission extending to the red region (−900 nm), since the luminescence color in a solid state can reversibly change due to their constrained structures granted by alkylene linkers and the choice of a proper counterion. X‐ray diffraction and spectroscopic analyses revealed that such mechanochromic behavior was induced by the crystal‐to‐amorphous transition. A change in the intermolecular interaction of macrocyclic dications 22+ would be the key to realizing a change in the emission pattern, since the color of the molecules did not change by applying mechanical stimuli. These findings may suggest a design strategy for creating a variety of stimuli‐responsive materials, especially for carbocation‐based fluorescent materials. Since triarylmethyliums absorb visible light, their emissions can be extended to longer wavelengths than their absorptions. The constrained structure of macrocyclic dications is the key to realizing the emission extending to the red region. Thus, tethered macrocyclic dications exhibit NIR‐mechanofluorochromism induced by the crystal‐to‐amorphous transition.
Bibliography:KAKEN
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ISSN:2192-6506
2192-6506
DOI:10.1002/cplu.202300110