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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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. |
doi_str_mv | 10.1039/d2tc00798c |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D2TC00798C</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2674373316</sourcerecordid><originalsourceid>FETCH-LOGICAL-c211t-913764d45ebf405309ee16cbcdaa47b2a4058723111cc1847120796fe56bcffb3</originalsourceid><addsrcrecordid>eNpFkc1KxDAUhYsoKOrGvRBwJ1bz06atOxkdFQQ3ui5pejMTaZMxNx2Y1_FJzTii2dxw-O45ISfLzhi9ZlQ0Nz2PmtKqqfVedsRpSfOqFMX-353Lw-wU8YOmUzNZy-Yo-3p1QOZERT-SUcUIAW8JblxcAlq8ImqxCLBQ0XqXW9dPGnoCo0VMAlGuJxjtOA02D4Ar79CuwQEi8YbEZQAgFv2YTLeCGSYf_I3xYdwMBKcu7cYpJscIMajVEtxmgJScntRDsOsUuwY8yQ6MGhBOf-dx9j5_eJs95S-vj8-zu5dcc8Zi3jBRyaIvSuhMQUtBGwAmdad7pYqq4yqJdcUFY0xrVhcV4-mvpIFSdtqYThxnFzvfVfCfE2BsP_wUXIpsuawKUQnBZKIud5QOHjGAaVfBjipsWkbbbQ3tPX-b_dQwS_D5Dg6o_7j_msQ3XZaJEA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2674373316</pqid></control><display><type>article</type><title>One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Li, Tianrui ; Miao, Jinling ; Xu, Chunyue ; Nie, Yong ; Liu, Wei ; Li, Yexin ; Liu, Guangning ; Jiang, Xuchuan</creator><creatorcontrib>Li, Tianrui ; Miao, Jinling ; Xu, Chunyue ; Nie, Yong ; Liu, Wei ; Li, Yexin ; Liu, Guangning ; Jiang, Xuchuan</creatorcontrib><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.</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. C, Materials for optical and electronic devices, 2022-06, Vol.1 (22), p.8657-8665</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c211t-913764d45ebf405309ee16cbcdaa47b2a4058723111cc1847120796fe56bcffb3</citedby><cites>FETCH-LOGICAL-c211t-913764d45ebf405309ee16cbcdaa47b2a4058723111cc1847120796fe56bcffb3</cites><orcidid>0000-0001-6998-9476 ; 0000-0003-2702-1744 ; 0000-0003-3311-5632 ; 0000-0001-8166-5490</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids></links><search><creatorcontrib>Li, Tianrui</creatorcontrib><creatorcontrib>Miao, Jinling</creatorcontrib><creatorcontrib>Xu, Chunyue</creatorcontrib><creatorcontrib>Nie, Yong</creatorcontrib><creatorcontrib>Liu, Wei</creatorcontrib><creatorcontrib>Li, Yexin</creatorcontrib><creatorcontrib>Liu, Guangning</creatorcontrib><creatorcontrib>Jiang, Xuchuan</creatorcontrib><title>One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives</title><title>Journal of materials chemistry. 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.
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><subject>Analogs</subject><subject>Chemical reactions</subject><subject>Composite materials</subject><subject>Cross coupling</subject><subject>Fluorescence</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Isomers</subject><subject>Luminescence</subject><subject>Optical properties</subject><subject>Organic compounds</subject><subject>Silica gel</subject><subject>Substitutes</subject><issn>2050-7526</issn><issn>2050-7534</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFkc1KxDAUhYsoKOrGvRBwJ1bz06atOxkdFQQ3ui5pejMTaZMxNx2Y1_FJzTii2dxw-O45ISfLzhi9ZlQ0Nz2PmtKqqfVedsRpSfOqFMX-353Lw-wU8YOmUzNZy-Yo-3p1QOZERT-SUcUIAW8JblxcAlq8ImqxCLBQ0XqXW9dPGnoCo0VMAlGuJxjtOA02D4Ar79CuwQEi8YbEZQAgFv2YTLeCGSYf_I3xYdwMBKcu7cYpJscIMajVEtxmgJScntRDsOsUuwY8yQ6MGhBOf-dx9j5_eJs95S-vj8-zu5dcc8Zi3jBRyaIvSuhMQUtBGwAmdad7pYqq4yqJdcUFY0xrVhcV4-mvpIFSdtqYThxnFzvfVfCfE2BsP_wUXIpsuawKUQnBZKIud5QOHjGAaVfBjipsWkbbbQ3tPX-b_dQwS_D5Dg6o_7j_msQ3XZaJEA</recordid><startdate>20220609</startdate><enddate>20220609</enddate><creator>Li, Tianrui</creator><creator>Miao, Jinling</creator><creator>Xu, Chunyue</creator><creator>Nie, Yong</creator><creator>Liu, Wei</creator><creator>Li, Yexin</creator><creator>Liu, Guangning</creator><creator>Jiang, Xuchuan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-6998-9476</orcidid><orcidid>https://orcid.org/0000-0003-2702-1744</orcidid><orcidid>https://orcid.org/0000-0003-3311-5632</orcidid><orcidid>https://orcid.org/0000-0001-8166-5490</orcidid></search><sort><creationdate>20220609</creationdate><title>One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives</title><author>Li, Tianrui ; Miao, Jinling ; Xu, Chunyue ; Nie, Yong ; Liu, Wei ; Li, Yexin ; Liu, Guangning ; Jiang, Xuchuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c211t-913764d45ebf405309ee16cbcdaa47b2a4058723111cc1847120796fe56bcffb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Analogs</topic><topic>Chemical reactions</topic><topic>Composite materials</topic><topic>Cross coupling</topic><topic>Fluorescence</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Isomers</topic><topic>Luminescence</topic><topic>Optical properties</topic><topic>Organic compounds</topic><topic>Silica gel</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Tianrui</creatorcontrib><creatorcontrib>Miao, Jinling</creatorcontrib><creatorcontrib>Xu, Chunyue</creatorcontrib><creatorcontrib>Nie, Yong</creatorcontrib><creatorcontrib>Liu, Wei</creatorcontrib><creatorcontrib>Li, Yexin</creatorcontrib><creatorcontrib>Liu, Guangning</creatorcontrib><creatorcontrib>Jiang, Xuchuan</creatorcontrib><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of materials chemistry. C, Materials for optical and electronic devices</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Tianrui</au><au>Miao, Jinling</au><au>Xu, Chunyue</au><au>Nie, Yong</au><au>Liu, Wei</au><au>Li, Yexin</au><au>Liu, Guangning</au><au>Jiang, Xuchuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One F atom matters: synthesis, aggregation-induced emission and stimuli-responsiveness of three isomers of fluoro/formyl substituted tetraphenylethene derivatives</atitle><jtitle>Journal of materials chemistry. 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
. 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.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2tc00798c</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-6998-9476</orcidid><orcidid>https://orcid.org/0000-0003-2702-1744</orcidid><orcidid>https://orcid.org/0000-0003-3311-5632</orcidid><orcidid>https://orcid.org/0000-0001-8166-5490</orcidid></addata></record> |
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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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