One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives

By introducing fluorine atom(s) into luminescent organic compounds, it may be possible to fine-tune their packing structure and luminescence properties. In the present work, three isomers of fluoro/formyl substituted tetraphenylethene (TPE) derivatives ( 1-3 ) with one fluorine atom have been synthe...

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Veröffentlicht in:Journal of materials chemistry. C, Materials for optical and electronic devices Materials for optical and electronic devices, 2022-06, Vol.1 (22), p.8657-8665
Hauptverfasser: Li, Tianrui, Miao, Jinling, Xu, Chunyue, Nie, Yong, Liu, Wei, Li, Yexin, Liu, Guangning, Jiang, Xuchuan
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container_issue 22
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container_title Journal of materials chemistry. C, Materials for optical and electronic devices
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creator Li, Tianrui
Miao, Jinling
Xu, Chunyue
Nie, Yong
Liu, Wei
Li, Yexin
Liu, Guangning
Jiang, Xuchuan
description By introducing fluorine atom(s) into luminescent organic compounds, it may be possible to fine-tune their packing structure and luminescence properties. In the present work, three isomers of fluoro/formyl substituted tetraphenylethene (TPE) derivatives ( 1-3 ) with one fluorine atom have been synthesized via the Suzuki-Miyaura cross-coupling reactions in high yields. With the different substitution positions of fluoro/formyl substituents, compounds 1-3 exhibit different luminescence behavior in THF/H 2 O mixed solvents and solid state, as well as responsiveness towards mechanical force and heat when compared with the non-fluorinated analogs TPE-4CHO , TPE-3CHO and TPE-2CHO . Compounds 1 and 3 exhibit mechanofluorochromism with red-shifted emissions, more drastic than those of TPE-4CHO and TPE-2CHO , while 2 and TPE-3CHO do not show this property under the same conditions. Compounds 1-3 all show thermofluorochromism with weaker and blue-shifted emissions on increasing temperatures, different from those of the non-fluorinated analogs, which only exhibit weaker emissions without a wavelength shift under the same conditions. Furthermore, the three compounds form composites with silica gel or filter paper strips, and the resulting composites show stronger and red-shifted emissions compared to the corresponding compounds, and also exhibit thermofluorochromism, which has potential in fluorescent thermometers and anti-counterfeiting. The luminescence properties of three fluorinated tetraphenylethene (TPE) derivatives indicate that the fluorine atom has a significant effect on the solid state packing, and thus the emissions and the stimuli-responsiveness.
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In the present work, three isomers of fluoro/formyl substituted tetraphenylethene (TPE) derivatives ( 1-3 ) with one fluorine atom have been synthesized via the Suzuki-Miyaura cross-coupling reactions in high yields. With the different substitution positions of fluoro/formyl substituents, compounds 1-3 exhibit different luminescence behavior in THF/H 2 O mixed solvents and solid state, as well as responsiveness towards mechanical force and heat when compared with the non-fluorinated analogs TPE-4CHO , TPE-3CHO and TPE-2CHO . Compounds 1 and 3 exhibit mechanofluorochromism with red-shifted emissions, more drastic than those of TPE-4CHO and TPE-2CHO , while 2 and TPE-3CHO do not show this property under the same conditions. Compounds 1-3 all show thermofluorochromism with weaker and blue-shifted emissions on increasing temperatures, different from those of the non-fluorinated analogs, which only exhibit weaker emissions without a wavelength shift under the same conditions. Furthermore, the three compounds form composites with silica gel or filter paper strips, and the resulting composites show stronger and red-shifted emissions compared to the corresponding compounds, and also exhibit thermofluorochromism, which has potential in fluorescent thermometers and anti-counterfeiting. The luminescence properties of three fluorinated tetraphenylethene (TPE) derivatives indicate that the fluorine atom has a significant effect on the solid state packing, and thus the emissions and the stimuli-responsiveness.</description><identifier>ISSN: 2050-7526</identifier><identifier>EISSN: 2050-7534</identifier><identifier>DOI: 10.1039/d2tc00798c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Analogs ; Chemical reactions ; Composite materials ; Cross coupling ; Fluorescence ; Fluorination ; Fluorine ; Isomers ; Luminescence ; Optical properties ; Organic compounds ; Silica gel ; Substitutes</subject><ispartof>Journal of materials chemistry. 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C, Materials for optical and electronic devices</title><description>By introducing fluorine atom(s) into luminescent organic compounds, it may be possible to fine-tune their packing structure and luminescence properties. In the present work, three isomers of fluoro/formyl substituted tetraphenylethene (TPE) derivatives ( 1-3 ) with one fluorine atom have been synthesized via the Suzuki-Miyaura cross-coupling reactions in high yields. With the different substitution positions of fluoro/formyl substituents, compounds 1-3 exhibit different luminescence behavior in THF/H 2 O mixed solvents and solid state, as well as responsiveness towards mechanical force and heat when compared with the non-fluorinated analogs TPE-4CHO , TPE-3CHO and TPE-2CHO . Compounds 1 and 3 exhibit mechanofluorochromism with red-shifted emissions, more drastic than those of TPE-4CHO and TPE-2CHO , while 2 and TPE-3CHO do not show this property under the same conditions. Compounds 1-3 all show thermofluorochromism with weaker and blue-shifted emissions on increasing temperatures, different from those of the non-fluorinated analogs, which only exhibit weaker emissions without a wavelength shift under the same conditions. Furthermore, the three compounds form composites with silica gel or filter paper strips, and the resulting composites show stronger and red-shifted emissions compared to the corresponding compounds, and also exhibit thermofluorochromism, which has potential in fluorescent thermometers and anti-counterfeiting. 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C, Materials for optical and electronic devices</jtitle><date>2022-06-09</date><risdate>2022</risdate><volume>1</volume><issue>22</issue><spage>8657</spage><epage>8665</epage><pages>8657-8665</pages><issn>2050-7526</issn><eissn>2050-7534</eissn><abstract>By introducing fluorine atom(s) into luminescent organic compounds, it may be possible to fine-tune their packing structure and luminescence properties. In the present work, three isomers of fluoro/formyl substituted tetraphenylethene (TPE) derivatives ( 1-3 ) with one fluorine atom have been synthesized via the Suzuki-Miyaura cross-coupling reactions in high yields. With the different substitution positions of fluoro/formyl substituents, compounds 1-3 exhibit different luminescence behavior in THF/H 2 O mixed solvents and solid state, as well as responsiveness towards mechanical force and heat when compared with the non-fluorinated analogs TPE-4CHO , TPE-3CHO and TPE-2CHO . 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source Royal Society Of Chemistry Journals 2008-
subjects Analogs
Chemical reactions
Composite materials
Cross coupling
Fluorescence
Fluorination
Fluorine
Isomers
Luminescence
Optical properties
Organic compounds
Silica gel
Substitutes
title One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives
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