Development of a novel colorimetric thermometer based on poly(-vinylcaprolactam) with push-π-pull tricyanofuran hydrazone anion dye
Thermochromic poly( N -vinylcaprolactam- co -tricyanofuran hydrazone) [poly(VC- co -TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. A novel vinyl-containing tricyanofuran hydrazone (TCFH) halochromic chromophore bearing a hydrazone senso...
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| Veröffentlicht in: | New journal of chemistry 2021-03, Vol.45 (12), p.5382-539 |
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| creator | Abdelrahman, Meram S Khattab, Tawfik A Kamel, Samir |
| description | Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. A novel vinyl-containing tricyanofuran hydrazone (TCFH) halochromic chromophore bearing a hydrazone sensor group was generated
via
an azo-coupling procedure of a tricyanofyran (TCF) heterocycle with the diazonium chloride salt of 2-hydroxy-4-nitroaniline comprising an allyl group. The molecular structures of the TCFH chromophore and related intermediates were proved by different techniques, including FT-IR, mass spectroscopy (MS),
1
H/
13
C NMR and elemental analyses (C, H, N). This chromophore showed a pronounced solvatochromic activity in various organic solvents of different polarities. pH sensing activity was also monitored at different pH values. Both solvatochromism and pH-responsiveness can be ascribed to the delocalization of charge on TCFH. Poly(VC-
co
-TCFH) acted as a thermochromic sensor device generating immediate colorimetric changes from yellow to orange, red, wine, violet, and purple with increasing temperature of aqueous poly(VC-
co
-TCFH) solution. Such colorimetric changes are proportionally interrelated with the temperature increase from 33 to 47 °C due to a phase change in an aqueous solution of poly(VC-
co
-TCFH) copolymer. The poly(VC-
co
-TCFH) copolymer composed of
N
-vinylcaprolactam (VC) and push-π-pull hydrazone type tricyanofuran chromophore monomers functions as a temperature-driven chromogenic thermometer. The morphology of the gel nanostructure was monitored by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Mechanistic studies accounting for solvatochromism and halochromism of TCFH as well as thermochromism of poly(VC-
co
-TCFH) are proposed.
Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. |
| doi_str_mv | 10.1039/d1nj00221j |
| format | Article |
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N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. A novel vinyl-containing tricyanofuran hydrazone (TCFH) halochromic chromophore bearing a hydrazone sensor group was generated
via
an azo-coupling procedure of a tricyanofyran (TCF) heterocycle with the diazonium chloride salt of 2-hydroxy-4-nitroaniline comprising an allyl group. The molecular structures of the TCFH chromophore and related intermediates were proved by different techniques, including FT-IR, mass spectroscopy (MS),
1
H/
13
C NMR and elemental analyses (C, H, N). This chromophore showed a pronounced solvatochromic activity in various organic solvents of different polarities. pH sensing activity was also monitored at different pH values. Both solvatochromism and pH-responsiveness can be ascribed to the delocalization of charge on TCFH. Poly(VC-
co
-TCFH) acted as a thermochromic sensor device generating immediate colorimetric changes from yellow to orange, red, wine, violet, and purple with increasing temperature of aqueous poly(VC-
co
-TCFH) solution. Such colorimetric changes are proportionally interrelated with the temperature increase from 33 to 47 °C due to a phase change in an aqueous solution of poly(VC-
co
-TCFH) copolymer. The poly(VC-
co
-TCFH) copolymer composed of
N
-vinylcaprolactam (VC) and push-π-pull hydrazone type tricyanofuran chromophore monomers functions as a temperature-driven chromogenic thermometer. The morphology of the gel nanostructure was monitored by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Mechanistic studies accounting for solvatochromism and halochromism of TCFH as well as thermochromism of poly(VC-
co
-TCFH) are proposed.
Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj00221j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aqueous solutions ; Chromophores ; Colorimetry ; Copolymers ; Coupling (molecular) ; Electron microscopy ; Free radical polymerization ; Free radicals ; Halochromism ; Hydrazones ; Infrared spectroscopy ; Microscopy ; Molecular structure ; Morphology ; NMR ; Nuclear magnetic resonance ; Thermochromism</subject><ispartof>New journal of chemistry, 2021-03, Vol.45 (12), p.5382-539</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-6694713acda0eb4c5aea55a17288c9b9d59e1852b06e2172d4df366bdf3296273</citedby><cites>FETCH-LOGICAL-c281t-6694713acda0eb4c5aea55a17288c9b9d59e1852b06e2172d4df366bdf3296273</cites><orcidid>0000-0001-7834-4952</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>Abdelrahman, Meram S</creatorcontrib><creatorcontrib>Khattab, Tawfik A</creatorcontrib><creatorcontrib>Kamel, Samir</creatorcontrib><title>Development of a novel colorimetric thermometer based on poly(-vinylcaprolactam) with push-π-pull tricyanofuran hydrazone anion dye</title><title>New journal of chemistry</title><description>Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. A novel vinyl-containing tricyanofuran hydrazone (TCFH) halochromic chromophore bearing a hydrazone sensor group was generated
via
an azo-coupling procedure of a tricyanofyran (TCF) heterocycle with the diazonium chloride salt of 2-hydroxy-4-nitroaniline comprising an allyl group. The molecular structures of the TCFH chromophore and related intermediates were proved by different techniques, including FT-IR, mass spectroscopy (MS),
1
H/
13
C NMR and elemental analyses (C, H, N). This chromophore showed a pronounced solvatochromic activity in various organic solvents of different polarities. pH sensing activity was also monitored at different pH values. Both solvatochromism and pH-responsiveness can be ascribed to the delocalization of charge on TCFH. Poly(VC-
co
-TCFH) acted as a thermochromic sensor device generating immediate colorimetric changes from yellow to orange, red, wine, violet, and purple with increasing temperature of aqueous poly(VC-
co
-TCFH) solution. Such colorimetric changes are proportionally interrelated with the temperature increase from 33 to 47 °C due to a phase change in an aqueous solution of poly(VC-
co
-TCFH) copolymer. The poly(VC-
co
-TCFH) copolymer composed of
N
-vinylcaprolactam (VC) and push-π-pull hydrazone type tricyanofuran chromophore monomers functions as a temperature-driven chromogenic thermometer. The morphology of the gel nanostructure was monitored by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Mechanistic studies accounting for solvatochromism and halochromism of TCFH as well as thermochromism of poly(VC-
co
-TCFH) are proposed.
Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization.</description><subject>Aqueous solutions</subject><subject>Chromophores</subject><subject>Colorimetry</subject><subject>Copolymers</subject><subject>Coupling (molecular)</subject><subject>Electron microscopy</subject><subject>Free radical polymerization</subject><subject>Free radicals</subject><subject>Halochromism</subject><subject>Hydrazones</subject><subject>Infrared spectroscopy</subject><subject>Microscopy</subject><subject>Molecular structure</subject><subject>Morphology</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Thermochromism</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkctKxDAUhosoOI5u3AsBNypEk7RNm6XMeBsG3ei6pElKO6RJTdqRunLh-_lKZhzRzbnx8Z_Df6LoGKNLjGJ2JbFZIUQIXu1EExxTBhmheDfUOEkgShO6Hx14HxiMM4on0edcrZW2XatMD2wFODA2DICw2rqmVb1rBOhr5VobGuVAyb2SwBrQWT2ewXVjRi1456zmouftOXhr-hp0g6_h1wfsBq3BRmPkxlaD4wbUo3T83RoFuGmCjhzVYbRXce3V0W-eRi-3N8-ze7h8unuYXS-hIDnuIaUsyXDMheRIlYlIueJpynFG8lywksmUKZynpERUkTCViaxiSssQCaMki6fR6VY3nPs6KN8XKzs4E1YWJEWU5ClCNFAXW0o4671TVdEFJ7gbC4yKjcvFHD8uflxeBPhkCzsv_rj_L8TfYfV8fw</recordid><startdate>20210329</startdate><enddate>20210329</enddate><creator>Abdelrahman, Meram S</creator><creator>Khattab, Tawfik A</creator><creator>Kamel, Samir</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-7834-4952</orcidid></search><sort><creationdate>20210329</creationdate><title>Development of a novel colorimetric thermometer based on poly(-vinylcaprolactam) with push-π-pull tricyanofuran hydrazone anion dye</title><author>Abdelrahman, Meram S ; Khattab, Tawfik A ; Kamel, Samir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-6694713acda0eb4c5aea55a17288c9b9d59e1852b06e2172d4df366bdf3296273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aqueous solutions</topic><topic>Chromophores</topic><topic>Colorimetry</topic><topic>Copolymers</topic><topic>Coupling (molecular)</topic><topic>Electron microscopy</topic><topic>Free radical polymerization</topic><topic>Free radicals</topic><topic>Halochromism</topic><topic>Hydrazones</topic><topic>Infrared spectroscopy</topic><topic>Microscopy</topic><topic>Molecular structure</topic><topic>Morphology</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Thermochromism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abdelrahman, Meram S</creatorcontrib><creatorcontrib>Khattab, Tawfik A</creatorcontrib><creatorcontrib>Kamel, Samir</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abdelrahman, Meram S</au><au>Khattab, Tawfik A</au><au>Kamel, Samir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Development of a novel colorimetric thermometer based on poly(-vinylcaprolactam) with push-π-pull tricyanofuran hydrazone anion dye</atitle><jtitle>New journal of chemistry</jtitle><date>2021-03-29</date><risdate>2021</risdate><volume>45</volume><issue>12</issue><spage>5382</spage><epage>539</epage><pages>5382-539</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization. A novel vinyl-containing tricyanofuran hydrazone (TCFH) halochromic chromophore bearing a hydrazone sensor group was generated
via
an azo-coupling procedure of a tricyanofyran (TCF) heterocycle with the diazonium chloride salt of 2-hydroxy-4-nitroaniline comprising an allyl group. The molecular structures of the TCFH chromophore and related intermediates were proved by different techniques, including FT-IR, mass spectroscopy (MS),
1
H/
13
C NMR and elemental analyses (C, H, N). This chromophore showed a pronounced solvatochromic activity in various organic solvents of different polarities. pH sensing activity was also monitored at different pH values. Both solvatochromism and pH-responsiveness can be ascribed to the delocalization of charge on TCFH. Poly(VC-
co
-TCFH) acted as a thermochromic sensor device generating immediate colorimetric changes from yellow to orange, red, wine, violet, and purple with increasing temperature of aqueous poly(VC-
co
-TCFH) solution. Such colorimetric changes are proportionally interrelated with the temperature increase from 33 to 47 °C due to a phase change in an aqueous solution of poly(VC-
co
-TCFH) copolymer. The poly(VC-
co
-TCFH) copolymer composed of
N
-vinylcaprolactam (VC) and push-π-pull hydrazone type tricyanofuran chromophore monomers functions as a temperature-driven chromogenic thermometer. The morphology of the gel nanostructure was monitored by transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Mechanistic studies accounting for solvatochromism and halochromism of TCFH as well as thermochromism of poly(VC-
co
-TCFH) are proposed.
Thermochromic poly(
N
-vinylcaprolactam-
co
-tricyanofuran hydrazone) [poly(VC-
co
-TCFH)] gel labeled with a halochromic chromophore was developed using traditional free radical polymerization.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj00221j</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-7834-4952</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | New journal of chemistry, 2021-03, Vol.45 (12), p.5382-539 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D1NJ00221J |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Aqueous solutions Chromophores Colorimetry Copolymers Coupling (molecular) Electron microscopy Free radical polymerization Free radicals Halochromism Hydrazones Infrared spectroscopy Microscopy Molecular structure Morphology NMR Nuclear magnetic resonance Thermochromism |
| title | Development of a novel colorimetric thermometer based on poly(-vinylcaprolactam) with push-π-pull tricyanofuran hydrazone anion dye |
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