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Synthesis of network polymer emitters: tunable detection of chemicals by geometric design
Conjugated network polymer emitters are potential materials for use as solid detectors of chemicals. We demonstrated the synthesis of fluorescent network polymers through a facile route. Solid-state fluorescent network polymer emitters were synthesized through the Knoevenagel polycondensation of an...
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| Published in: | Polymer journal 2019-10, Vol.51 (10), p.1055-1061 |
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| container_end_page | 1061 |
| container_issue | 10 |
| container_start_page | 1055 |
| container_title | Polymer journal |
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| creator | Hayashi, Shotaro Yamamoto, Shin-ichi Nishi, Koji Asano, Atsushi Koizumi, Toshio |
| description | Conjugated network polymer emitters are potential materials for use as solid detectors of chemicals. We demonstrated the synthesis of fluorescent network polymers through a facile route. Solid-state fluorescent network polymer emitters were synthesized through the Knoevenagel polycondensation of an arylaldehyde (tris(
p
-formylphenyl)amine) with an arylacetonitrile (phenylenediacetonitrile) in good yields. The molecular structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The synthesized model small molecule showed a well-defined solvatofluorochromism: the dielectric constants were
ε
sol
of approximately 0–50 at
λ
fl
of 480–560 nm. The response to solvent chemicals was also shown for the network polymers. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant (
ε
sol
ca. |
| doi_str_mv | 10.1038/s41428-019-0216-1 |
| format | article |
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p
-formylphenyl)amine) with an arylacetonitrile (phenylenediacetonitrile) in good yields. The molecular structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The synthesized model small molecule showed a well-defined solvatofluorochromism: the dielectric constants were
ε
sol
of approximately 0–50 at
λ
fl
of 480–560 nm. The response to solvent chemicals was also shown for the network polymers. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant (
ε
sol
ca. <8) and nitrobenzene, for which
ε
sol
is approximately 35. This solvatofluorochromic behavior differed from that of the model compound. More interestingly, the network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. Consequently, the characteristic chemoselectivity was observed by the geometric effect of the network structure.
We demonstrated the synthesis of fluorescent network polymers through Knoevenagel polycondensation of an (tris(
p
-formylphenyl)amine) with a phenylenediacetonitrile. The structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The model molecule showed a well-defined solvatofluorochromism. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant and nitrobenzene. The network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. The characteristic chemoselectivity was observed by the geometric effect of the network structure.</description><identifier>ISSN: 0032-3896</identifier><identifier>EISSN: 1349-0540</identifier><identifier>DOI: 10.1038/s41428-019-0216-1</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>140/131 ; 639/638/455/941 ; 639/638/455/954 ; Biomaterials ; Bioorganic Chemistry ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Emitters ; Emitters (electron) ; Fluorescence ; Molecular structure ; Organic chemistry ; Original Article ; Permittivity ; Polymer Sciences ; Polymers ; Solid state ; Solvents ; Surfaces and Interfaces ; Thin Films</subject><ispartof>Polymer journal, 2019-10, Vol.51 (10), p.1055-1061</ispartof><rights>The Society of Polymer Science, Japan 2019</rights><rights>The Society of Polymer Science, Japan 2019.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c409t-e85eb2dc76dc1d2db99652cef1e483ee3dd62b8e5f44e82cf242dcade90de9c13</citedby><cites>FETCH-LOGICAL-c409t-e85eb2dc76dc1d2db99652cef1e483ee3dd62b8e5f44e82cf242dcade90de9c13</cites><orcidid>0000-0001-8017-2395 ; 0000-0003-1311-3680 ; 0000-0001-8703-6740</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Hayashi, Shotaro</creatorcontrib><creatorcontrib>Yamamoto, Shin-ichi</creatorcontrib><creatorcontrib>Nishi, Koji</creatorcontrib><creatorcontrib>Asano, Atsushi</creatorcontrib><creatorcontrib>Koizumi, Toshio</creatorcontrib><title>Synthesis of network polymer emitters: tunable detection of chemicals by geometric design</title><title>Polymer journal</title><addtitle>Polym J</addtitle><description>Conjugated network polymer emitters are potential materials for use as solid detectors of chemicals. We demonstrated the synthesis of fluorescent network polymers through a facile route. Solid-state fluorescent network polymer emitters were synthesized through the Knoevenagel polycondensation of an arylaldehyde (tris(
p
-formylphenyl)amine) with an arylacetonitrile (phenylenediacetonitrile) in good yields. The molecular structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The synthesized model small molecule showed a well-defined solvatofluorochromism: the dielectric constants were
ε
sol
of approximately 0–50 at
λ
fl
of 480–560 nm. The response to solvent chemicals was also shown for the network polymers. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant (
ε
sol
ca. <8) and nitrobenzene, for which
ε
sol
is approximately 35. This solvatofluorochromic behavior differed from that of the model compound. More interestingly, the network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. Consequently, the characteristic chemoselectivity was observed by the geometric effect of the network structure.
We demonstrated the synthesis of fluorescent network polymers through Knoevenagel polycondensation of an (tris(
p
-formylphenyl)amine) with a phenylenediacetonitrile. The structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The model molecule showed a well-defined solvatofluorochromism. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant and nitrobenzene. The network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. The characteristic chemoselectivity was observed by the geometric effect of the network structure.</description><subject>140/131</subject><subject>639/638/455/941</subject><subject>639/638/455/954</subject><subject>Biomaterials</subject><subject>Bioorganic Chemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Emitters</subject><subject>Emitters (electron)</subject><subject>Fluorescence</subject><subject>Molecular structure</subject><subject>Organic chemistry</subject><subject>Original Article</subject><subject>Permittivity</subject><subject>Polymer Sciences</subject><subject>Polymers</subject><subject>Solid state</subject><subject>Solvents</subject><subject>Surfaces and Interfaces</subject><subject>Thin Films</subject><issn>0032-3896</issn><issn>1349-0540</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LxDAQxYMouK5-AG8Bz9H8a028yaKrsOBBPXgKbTLd7bpt1iSL9NubUsGTDMMwzO-9gYfQJaPXjAp1EyWTXBHKNKGclYQdoRkTMm-FpMdoRqngRChdnqKzGLeU8rKgcoY-Xoc-bSC2EfsG95C-ffjEe78bOggYujYlCPEOp0Nf1TvADhLY1Pp-xO0mA7baRVwPeA2-gxRam5nYrvtzdNLkE1z8zjl6f3x4WzyR1cvyeXG_IlZSnQioAmru7G3pLHPc1VqXBbfQMJBKAAjnSl4rKBopQXHbcJnpyoGmuS0Tc3Q1-e6D_zpATGbrD6HPLw3nOpfUSmeKTZQNPsYAjdmHtqvCYBg1Y4JmStDkBM2YoBmd-aSJme3XEP6c_xf9AISZdeg</recordid><startdate>20191001</startdate><enddate>20191001</enddate><creator>Hayashi, Shotaro</creator><creator>Yamamoto, Shin-ichi</creator><creator>Nishi, Koji</creator><creator>Asano, Atsushi</creator><creator>Koizumi, Toshio</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><orcidid>https://orcid.org/0000-0001-8017-2395</orcidid><orcidid>https://orcid.org/0000-0003-1311-3680</orcidid><orcidid>https://orcid.org/0000-0001-8703-6740</orcidid></search><sort><creationdate>20191001</creationdate><title>Synthesis of network polymer emitters: tunable detection of chemicals by geometric design</title><author>Hayashi, Shotaro ; Yamamoto, Shin-ichi ; Nishi, Koji ; Asano, Atsushi ; Koizumi, Toshio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c409t-e85eb2dc76dc1d2db99652cef1e483ee3dd62b8e5f44e82cf242dcade90de9c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>140/131</topic><topic>639/638/455/941</topic><topic>639/638/455/954</topic><topic>Biomaterials</topic><topic>Bioorganic Chemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Emitters</topic><topic>Emitters (electron)</topic><topic>Fluorescence</topic><topic>Molecular structure</topic><topic>Organic chemistry</topic><topic>Original Article</topic><topic>Permittivity</topic><topic>Polymer Sciences</topic><topic>Polymers</topic><topic>Solid state</topic><topic>Solvents</topic><topic>Surfaces and Interfaces</topic><topic>Thin Films</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hayashi, Shotaro</creatorcontrib><creatorcontrib>Yamamoto, Shin-ichi</creatorcontrib><creatorcontrib>Nishi, Koji</creatorcontrib><creatorcontrib>Asano, Atsushi</creatorcontrib><creatorcontrib>Koizumi, Toshio</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><jtitle>Polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hayashi, Shotaro</au><au>Yamamoto, Shin-ichi</au><au>Nishi, Koji</au><au>Asano, Atsushi</au><au>Koizumi, Toshio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of network polymer emitters: tunable detection of chemicals by geometric design</atitle><jtitle>Polymer journal</jtitle><stitle>Polym J</stitle><date>2019-10-01</date><risdate>2019</risdate><volume>51</volume><issue>10</issue><spage>1055</spage><epage>1061</epage><pages>1055-1061</pages><issn>0032-3896</issn><eissn>1349-0540</eissn><abstract>Conjugated network polymer emitters are potential materials for use as solid detectors of chemicals. We demonstrated the synthesis of fluorescent network polymers through a facile route. Solid-state fluorescent network polymer emitters were synthesized through the Knoevenagel polycondensation of an arylaldehyde (tris(
p
-formylphenyl)amine) with an arylacetonitrile (phenylenediacetonitrile) in good yields. The molecular structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The synthesized model small molecule showed a well-defined solvatofluorochromism: the dielectric constants were
ε
sol
of approximately 0–50 at
λ
fl
of 480–560 nm. The response to solvent chemicals was also shown for the network polymers. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant (
ε
sol
ca. <8) and nitrobenzene, for which
ε
sol
is approximately 35. This solvatofluorochromic behavior differed from that of the model compound. More interestingly, the network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. Consequently, the characteristic chemoselectivity was observed by the geometric effect of the network structure.
We demonstrated the synthesis of fluorescent network polymers through Knoevenagel polycondensation of an (tris(
p
-formylphenyl)amine) with a phenylenediacetonitrile. The structure based on the electron-donor triphenylamine and electron-acceptor cyano-substituted phenylene-vinylene showed a highly efficient solid-state fluorescence. The model molecule showed a well-defined solvatofluorochromism. Surprisingly, the network polymer linked with
para
-phenylene-vinylene was only responsive to the solvents with a low dielectric constant and nitrobenzene. The network polymer linked with
meta
-phenylene-vinylene was responsive to the aromatic solvents only. The characteristic chemoselectivity was observed by the geometric effect of the network structure.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><doi>10.1038/s41428-019-0216-1</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-8017-2395</orcidid><orcidid>https://orcid.org/0000-0003-1311-3680</orcidid><orcidid>https://orcid.org/0000-0001-8703-6740</orcidid></addata></record> |
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| subjects | 140/131 639/638/455/941 639/638/455/954 Biomaterials Bioorganic Chemistry Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Emitters Emitters (electron) Fluorescence Molecular structure Organic chemistry Original Article Permittivity Polymer Sciences Polymers Solid state Solvents Surfaces and Interfaces Thin Films |
| title | Synthesis of network polymer emitters: tunable detection of chemicals by geometric design |
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