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Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives
Due to the sensitivity for interchanging color by exposure to UV light, designing of fluorescent textiles is highly demanded to be employed in camping, military and sensing purposes. Aromatic compounds containing tetrahydroisoquinoline are known with their biological and medicinal activity, but they...
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| Published in: | Cellulose (London) 2021-06, Vol.28 (9), p.5937-5956 |
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| creator | Marae, Islam S. Sharmoukh, Walid Bakhite, Etify A. Moustafa, Osama Sh Abbady, Mohamed S. Emam, Hossam E. |
| description | Due to the sensitivity for interchanging color by exposure to UV light, designing of fluorescent textiles is highly demanded to be employed in camping, military and sensing purposes. Aromatic compounds containing tetrahydroisoquinoline are known with their biological and medicinal activity, but they are not applied as fluorescent materials. Therefore, the present study focuses on synthesis of tetrahydrothienoisoquinoline derivatives and their application in textile technology to obtain fluorescent cotton fabrics. Four tetrahydrothienoisoquinoline derivatives were synthesized in three steps, starting from 2,4-diacetyl-5-hydroxy-5-methyl-3-(4-methoxyphenyl)cyclohexanone. The chemical structures of the synthesized tetrahydrothienoisoquinoline derivatives (Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
) were confirmed by infrared spectra,
1
HNMR and
13
CNMR. The yields and melting points were both measured for all the synthesized compounds. The tetrahydrothienoisoquinoline derivatives were applied onto the cotton fabrics to obtain Ar1-Ph@cotton, Ar2-Ph-Cl@cotton, Ar3-Ph-CH
3
@cotton and Ar4-Ph-OCH
3
@cotton fabrics. All modified cotton fabrics were exhibited by green emission under UV lamp (325 nm). The excited modified cotton fabrics showed an intense fluorescence emission peak at 444–467 nm, related to the implemented compounds. The intensity of the fluorescence peak followed the order of Ar1-Ph@cotton > Ar3-Ph-CH
3
@cotton ≥ Ar4-Ph-OCH
3
@cotton >> Ar2-Ph-Cl@cotton. The estimated quantum yield (QY) were 68.79%, 23.15%, 13.83% and 13.38%, for Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
, respectively. Due to the water insoluble character of tetrahydrothienoisoquinoline derivatives, the modified fabrics showed quite good durability, as the the quantum yields were marginally diminished by only 10.1 – 12.3%, after 5 washings. The prepared tetrahydrothienoisoquinoline derivatives succeeded for obtaining durable fluorescent textiles, and could be further applied in advanced purposes including technical textiles, sensors/biosensors, smart labeling and anti-counterfeiting purposes.
Graphic abstract |
| doi_str_mv | 10.1007/s10570-021-03871-1 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2533992553</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2533992553</sourcerecordid><originalsourceid>FETCH-LOGICAL-c356t-bb17d66e489a91ca8e8db4b0c8c73ab21e0d478b0fcbac8f60354fa3edad0f5f3</originalsourceid><addsrcrecordid>eNp9kEtLAzEUhYMoWKt_wNWA69GbyTwyS6lPKLhRcBeSzE2bMp20SaZYf73RCu5cncU537mXQ8glhWsK0NwEClUDORQ0B8YbmtMjMqFVU-ScF-_HZAJt3SabtafkLIQVALRNQSdkcTd6qXrMTD86j0HjEDPtYnRDFvEj2mSpfWbXa6dsbz9ltMlxJhsHux0xZaKXy33nXVxaHJwNbjvawfV2wKxDb3eJ2GE4JydG9gEvfnVK3h7uX2dP-fzl8Xl2O881q-qYK0Wbrq6x5K1sqZYceadKBZrrhklVUISubLgCo5XU3NTAqtJIhp3swFSGTcnVoXfj0yMYoli50Q_ppCgqxtq2qJJMSXFIae9C8GjExtu19HtBQXwPKg6DijSo-BlU0ASxAxRSeFig_6v-h_oCgm99dA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2533992553</pqid></control><display><type>article</type><title>Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives</title><source>Springer Link</source><creator>Marae, Islam S. ; Sharmoukh, Walid ; Bakhite, Etify A. ; Moustafa, Osama Sh ; Abbady, Mohamed S. ; Emam, Hossam E.</creator><creatorcontrib>Marae, Islam S. ; Sharmoukh, Walid ; Bakhite, Etify A. ; Moustafa, Osama Sh ; Abbady, Mohamed S. ; Emam, Hossam E.</creatorcontrib><description>Due to the sensitivity for interchanging color by exposure to UV light, designing of fluorescent textiles is highly demanded to be employed in camping, military and sensing purposes. Aromatic compounds containing tetrahydroisoquinoline are known with their biological and medicinal activity, but they are not applied as fluorescent materials. Therefore, the present study focuses on synthesis of tetrahydrothienoisoquinoline derivatives and their application in textile technology to obtain fluorescent cotton fabrics. Four tetrahydrothienoisoquinoline derivatives were synthesized in three steps, starting from 2,4-diacetyl-5-hydroxy-5-methyl-3-(4-methoxyphenyl)cyclohexanone. The chemical structures of the synthesized tetrahydrothienoisoquinoline derivatives (Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
) were confirmed by infrared spectra,
1
HNMR and
13
CNMR. The yields and melting points were both measured for all the synthesized compounds. The tetrahydrothienoisoquinoline derivatives were applied onto the cotton fabrics to obtain Ar1-Ph@cotton, Ar2-Ph-Cl@cotton, Ar3-Ph-CH
3
@cotton and Ar4-Ph-OCH
3
@cotton fabrics. All modified cotton fabrics were exhibited by green emission under UV lamp (325 nm). The excited modified cotton fabrics showed an intense fluorescence emission peak at 444–467 nm, related to the implemented compounds. The intensity of the fluorescence peak followed the order of Ar1-Ph@cotton > Ar3-Ph-CH
3
@cotton ≥ Ar4-Ph-OCH
3
@cotton >> Ar2-Ph-Cl@cotton. The estimated quantum yield (QY) were 68.79%, 23.15%, 13.83% and 13.38%, for Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
, respectively. Due to the water insoluble character of tetrahydrothienoisoquinoline derivatives, the modified fabrics showed quite good durability, as the the quantum yields were marginally diminished by only 10.1 – 12.3%, after 5 washings. The prepared tetrahydrothienoisoquinoline derivatives succeeded for obtaining durable fluorescent textiles, and could be further applied in advanced purposes including technical textiles, sensors/biosensors, smart labeling and anti-counterfeiting purposes.
Graphic abstract</description><identifier>ISSN: 0969-0239</identifier><identifier>EISSN: 1572-882X</identifier><identifier>DOI: 10.1007/s10570-021-03871-1</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Aromatic compounds ; Biological activity ; Bioorganic Chemistry ; Biosensors ; Ceramics ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Color sensitivity ; Composites ; Cotton ; Cotton fabrics ; Cyclohexanone ; Durability ; Exchanging ; Fabrics ; Fluorescence ; Glass ; Industrial textiles ; Infrared spectra ; Melting points ; Natural Materials ; Organic Chemistry ; Original Research ; Physical Chemistry ; Polymer Sciences ; Smart sensors ; Sustainable Development ; Textiles ; Ultraviolet radiation</subject><ispartof>Cellulose (London), 2021-06, Vol.28 (9), p.5937-5956</ispartof><rights>The Author(s), under exclusive licence to Springer Nature B.V. 2021</rights><rights>The Author(s), under exclusive licence to Springer Nature B.V. 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-bb17d66e489a91ca8e8db4b0c8c73ab21e0d478b0fcbac8f60354fa3edad0f5f3</citedby><cites>FETCH-LOGICAL-c356t-bb17d66e489a91ca8e8db4b0c8c73ab21e0d478b0fcbac8f60354fa3edad0f5f3</cites><orcidid>0000-0002-5512-935X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids></links><search><creatorcontrib>Marae, Islam S.</creatorcontrib><creatorcontrib>Sharmoukh, Walid</creatorcontrib><creatorcontrib>Bakhite, Etify A.</creatorcontrib><creatorcontrib>Moustafa, Osama Sh</creatorcontrib><creatorcontrib>Abbady, Mohamed S.</creatorcontrib><creatorcontrib>Emam, Hossam E.</creatorcontrib><title>Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives</title><title>Cellulose (London)</title><addtitle>Cellulose</addtitle><description>Due to the sensitivity for interchanging color by exposure to UV light, designing of fluorescent textiles is highly demanded to be employed in camping, military and sensing purposes. Aromatic compounds containing tetrahydroisoquinoline are known with their biological and medicinal activity, but they are not applied as fluorescent materials. Therefore, the present study focuses on synthesis of tetrahydrothienoisoquinoline derivatives and their application in textile technology to obtain fluorescent cotton fabrics. Four tetrahydrothienoisoquinoline derivatives were synthesized in three steps, starting from 2,4-diacetyl-5-hydroxy-5-methyl-3-(4-methoxyphenyl)cyclohexanone. The chemical structures of the synthesized tetrahydrothienoisoquinoline derivatives (Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
) were confirmed by infrared spectra,
1
HNMR and
13
CNMR. The yields and melting points were both measured for all the synthesized compounds. The tetrahydrothienoisoquinoline derivatives were applied onto the cotton fabrics to obtain Ar1-Ph@cotton, Ar2-Ph-Cl@cotton, Ar3-Ph-CH
3
@cotton and Ar4-Ph-OCH
3
@cotton fabrics. All modified cotton fabrics were exhibited by green emission under UV lamp (325 nm). The excited modified cotton fabrics showed an intense fluorescence emission peak at 444–467 nm, related to the implemented compounds. The intensity of the fluorescence peak followed the order of Ar1-Ph@cotton > Ar3-Ph-CH
3
@cotton ≥ Ar4-Ph-OCH
3
@cotton >> Ar2-Ph-Cl@cotton. The estimated quantum yield (QY) were 68.79%, 23.15%, 13.83% and 13.38%, for Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
, respectively. Due to the water insoluble character of tetrahydrothienoisoquinoline derivatives, the modified fabrics showed quite good durability, as the the quantum yields were marginally diminished by only 10.1 – 12.3%, after 5 washings. The prepared tetrahydrothienoisoquinoline derivatives succeeded for obtaining durable fluorescent textiles, and could be further applied in advanced purposes including technical textiles, sensors/biosensors, smart labeling and anti-counterfeiting purposes.
Graphic abstract</description><subject>Aromatic compounds</subject><subject>Biological activity</subject><subject>Bioorganic Chemistry</subject><subject>Biosensors</subject><subject>Ceramics</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Color sensitivity</subject><subject>Composites</subject><subject>Cotton</subject><subject>Cotton fabrics</subject><subject>Cyclohexanone</subject><subject>Durability</subject><subject>Exchanging</subject><subject>Fabrics</subject><subject>Fluorescence</subject><subject>Glass</subject><subject>Industrial textiles</subject><subject>Infrared spectra</subject><subject>Melting points</subject><subject>Natural Materials</subject><subject>Organic Chemistry</subject><subject>Original Research</subject><subject>Physical Chemistry</subject><subject>Polymer Sciences</subject><subject>Smart sensors</subject><subject>Sustainable Development</subject><subject>Textiles</subject><subject>Ultraviolet radiation</subject><issn>0969-0239</issn><issn>1572-882X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhYMoWKt_wNWA69GbyTwyS6lPKLhRcBeSzE2bMp20SaZYf73RCu5cncU537mXQ8glhWsK0NwEClUDORQ0B8YbmtMjMqFVU-ScF-_HZAJt3SabtafkLIQVALRNQSdkcTd6qXrMTD86j0HjEDPtYnRDFvEj2mSpfWbXa6dsbz9ltMlxJhsHux0xZaKXy33nXVxaHJwNbjvawfV2wKxDb3eJ2GE4JydG9gEvfnVK3h7uX2dP-fzl8Xl2O881q-qYK0Wbrq6x5K1sqZYceadKBZrrhklVUISubLgCo5XU3NTAqtJIhp3swFSGTcnVoXfj0yMYoli50Q_ppCgqxtq2qJJMSXFIae9C8GjExtu19HtBQXwPKg6DijSo-BlU0ASxAxRSeFig_6v-h_oCgm99dA</recordid><startdate>20210601</startdate><enddate>20210601</enddate><creator>Marae, Islam S.</creator><creator>Sharmoukh, Walid</creator><creator>Bakhite, Etify A.</creator><creator>Moustafa, Osama Sh</creator><creator>Abbady, Mohamed S.</creator><creator>Emam, Hossam E.</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</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>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><orcidid>https://orcid.org/0000-0002-5512-935X</orcidid></search><sort><creationdate>20210601</creationdate><title>Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives</title><author>Marae, Islam S. ; Sharmoukh, Walid ; Bakhite, Etify A. ; Moustafa, Osama Sh ; Abbady, Mohamed S. ; Emam, Hossam E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-bb17d66e489a91ca8e8db4b0c8c73ab21e0d478b0fcbac8f60354fa3edad0f5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>Biological activity</topic><topic>Bioorganic Chemistry</topic><topic>Biosensors</topic><topic>Ceramics</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Color sensitivity</topic><topic>Composites</topic><topic>Cotton</topic><topic>Cotton fabrics</topic><topic>Cyclohexanone</topic><topic>Durability</topic><topic>Exchanging</topic><topic>Fabrics</topic><topic>Fluorescence</topic><topic>Glass</topic><topic>Industrial textiles</topic><topic>Infrared spectra</topic><topic>Melting points</topic><topic>Natural Materials</topic><topic>Organic Chemistry</topic><topic>Original Research</topic><topic>Physical Chemistry</topic><topic>Polymer Sciences</topic><topic>Smart sensors</topic><topic>Sustainable Development</topic><topic>Textiles</topic><topic>Ultraviolet radiation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marae, Islam S.</creatorcontrib><creatorcontrib>Sharmoukh, Walid</creatorcontrib><creatorcontrib>Bakhite, Etify A.</creatorcontrib><creatorcontrib>Moustafa, Osama Sh</creatorcontrib><creatorcontrib>Abbady, Mohamed S.</creatorcontrib><creatorcontrib>Emam, Hossam E.</creatorcontrib><collection>CrossRef</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 Korea</collection><collection>SciTech Premium Collection (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest 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><jtitle>Cellulose (London)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marae, Islam S.</au><au>Sharmoukh, Walid</au><au>Bakhite, Etify A.</au><au>Moustafa, Osama Sh</au><au>Abbady, Mohamed S.</au><au>Emam, Hossam E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives</atitle><jtitle>Cellulose (London)</jtitle><stitle>Cellulose</stitle><date>2021-06-01</date><risdate>2021</risdate><volume>28</volume><issue>9</issue><spage>5937</spage><epage>5956</epage><pages>5937-5956</pages><issn>0969-0239</issn><eissn>1572-882X</eissn><abstract>Due to the sensitivity for interchanging color by exposure to UV light, designing of fluorescent textiles is highly demanded to be employed in camping, military and sensing purposes. Aromatic compounds containing tetrahydroisoquinoline are known with their biological and medicinal activity, but they are not applied as fluorescent materials. Therefore, the present study focuses on synthesis of tetrahydrothienoisoquinoline derivatives and their application in textile technology to obtain fluorescent cotton fabrics. Four tetrahydrothienoisoquinoline derivatives were synthesized in three steps, starting from 2,4-diacetyl-5-hydroxy-5-methyl-3-(4-methoxyphenyl)cyclohexanone. The chemical structures of the synthesized tetrahydrothienoisoquinoline derivatives (Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
) were confirmed by infrared spectra,
1
HNMR and
13
CNMR. The yields and melting points were both measured for all the synthesized compounds. The tetrahydrothienoisoquinoline derivatives were applied onto the cotton fabrics to obtain Ar1-Ph@cotton, Ar2-Ph-Cl@cotton, Ar3-Ph-CH
3
@cotton and Ar4-Ph-OCH
3
@cotton fabrics. All modified cotton fabrics were exhibited by green emission under UV lamp (325 nm). The excited modified cotton fabrics showed an intense fluorescence emission peak at 444–467 nm, related to the implemented compounds. The intensity of the fluorescence peak followed the order of Ar1-Ph@cotton > Ar3-Ph-CH
3
@cotton ≥ Ar4-Ph-OCH
3
@cotton >> Ar2-Ph-Cl@cotton. The estimated quantum yield (QY) were 68.79%, 23.15%, 13.83% and 13.38%, for Ar1-Ph, Ar2-Ph-Cl, Ar3-Ph-CH
3
and Ar4-Ph-OCH
3
, respectively. Due to the water insoluble character of tetrahydrothienoisoquinoline derivatives, the modified fabrics showed quite good durability, as the the quantum yields were marginally diminished by only 10.1 – 12.3%, after 5 washings. The prepared tetrahydrothienoisoquinoline derivatives succeeded for obtaining durable fluorescent textiles, and could be further applied in advanced purposes including technical textiles, sensors/biosensors, smart labeling and anti-counterfeiting purposes.
Graphic abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s10570-021-03871-1</doi><tpages>20</tpages><orcidid>https://orcid.org/0000-0002-5512-935X</orcidid></addata></record> |
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| subjects | Aromatic compounds Biological activity Bioorganic Chemistry Biosensors Ceramics Chemical synthesis Chemistry Chemistry and Materials Science Color sensitivity Composites Cotton Cotton fabrics Cyclohexanone Durability Exchanging Fabrics Fluorescence Glass Industrial textiles Infrared spectra Melting points Natural Materials Organic Chemistry Original Research Physical Chemistry Polymer Sciences Smart sensors Sustainable Development Textiles Ultraviolet radiation |
| title | Durable fluorescent cotton textile by immobilization of unique tetrahydrothienoisoquinoline derivatives |
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