Synthesis and applications of some new nitrogen-containing heterocyclic azo-disperse dyes bearing quinoline chromophore
A set of five novel nitrogen-containing heterocyclic azo-disperse dyes 8 (a–d) and 10 were synthesized by diazotization of 4-bisaminoquinolines 3 , followed by coupling either with rhodanine analogues 6 modified at C-5 position or α-naphthol 9 . The chemical structures of 8(a–d) and 10 were proven b...
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| Veröffentlicht in: | Journal of the Iranian Chemical Society 2022, Vol.19 (1), p.147-158 |
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| creator | Hassan, Khalid Mahmoud ElKhabiery, Shaban Abdel Sattar ElHaddad, Ghada Mahmoud Shokair, Sameha Hassan ElSayed, Ibrahim ElTantawy |
| description | A set of five novel nitrogen-containing heterocyclic azo-disperse dyes
8 (a–d)
and
10
were synthesized by diazotization of 4-bisaminoquinolines
3
, followed by coupling either with rhodanine analogues
6
modified at C-5 position or α-naphthol
9
. The chemical structures of
8(a–d)
and
10
were proven by the FT-IR, NMR, and mass spectroscopic techniques. Moreover, utilization of these azo dyes in preparing pastes for printing polyester fabric by silk screen traditional printing was achieved. The color strength and fastness properties of the synthesized dyes were also examined and showed moderate-to-excellent resistance to washing, rubbing, and perspiration, as well as fastness to sublimation and light. In addition, the targeted printed samples were screened for their in vitro antibacterial activity against both Gram-positive and Gram-negative bacterial species. The azo compound
8a
showed the best antibacterial activity against
S. aureus
with inhibition zone of 23 mm which is higher than the reference drug Ampicillin (21 mm). |
| doi_str_mv | 10.1007/s13738-021-02294-w |
| format | Article |
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8 (a–d)
and
10
were synthesized by diazotization of 4-bisaminoquinolines
3
, followed by coupling either with rhodanine analogues
6
modified at C-5 position or α-naphthol
9
. The chemical structures of
8(a–d)
and
10
were proven by the FT-IR, NMR, and mass spectroscopic techniques. Moreover, utilization of these azo dyes in preparing pastes for printing polyester fabric by silk screen traditional printing was achieved. The color strength and fastness properties of the synthesized dyes were also examined and showed moderate-to-excellent resistance to washing, rubbing, and perspiration, as well as fastness to sublimation and light. In addition, the targeted printed samples were screened for their in vitro antibacterial activity against both Gram-positive and Gram-negative bacterial species. The azo compound
8a
showed the best antibacterial activity against
S. aureus
with inhibition zone of 23 mm which is higher than the reference drug Ampicillin (21 mm).</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-021-02294-w</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Ampicillin ; Analytical Chemistry ; Azo compounds ; Biochemistry ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chromophores ; Dispersion ; Dyes ; Inorganic Chemistry ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Original Paper ; Pastes ; Perspiration ; Physical Chemistry ; Quinoline ; Rubbing ; Silk ; Sublimation</subject><ispartof>Journal of the Iranian Chemical Society, 2022, Vol.19 (1), p.147-158</ispartof><rights>Iranian Chemical Society 2021</rights><rights>Iranian Chemical Society 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-165dd9666c8f42701dc609fb4e915f6a39208e4f8f51d414db4bc4fe34bc83e43</citedby><cites>FETCH-LOGICAL-c319t-165dd9666c8f42701dc609fb4e915f6a39208e4f8f51d414db4bc4fe34bc83e43</cites><orcidid>0000-0003-1227-7931 ; 0000-0001-6334-4423</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13738-021-02294-w$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-021-02294-w$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27929,27930,41493,42562,51324</link.rule.ids></links><search><creatorcontrib>Hassan, Khalid Mahmoud</creatorcontrib><creatorcontrib>ElKhabiery, Shaban Abdel Sattar</creatorcontrib><creatorcontrib>ElHaddad, Ghada Mahmoud</creatorcontrib><creatorcontrib>Shokair, Sameha Hassan</creatorcontrib><creatorcontrib>ElSayed, Ibrahim ElTantawy</creatorcontrib><title>Synthesis and applications of some new nitrogen-containing heterocyclic azo-disperse dyes bearing quinoline chromophore</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>A set of five novel nitrogen-containing heterocyclic azo-disperse dyes
8 (a–d)
and
10
were synthesized by diazotization of 4-bisaminoquinolines
3
, followed by coupling either with rhodanine analogues
6
modified at C-5 position or α-naphthol
9
. The chemical structures of
8(a–d)
and
10
were proven by the FT-IR, NMR, and mass spectroscopic techniques. Moreover, utilization of these azo dyes in preparing pastes for printing polyester fabric by silk screen traditional printing was achieved. The color strength and fastness properties of the synthesized dyes were also examined and showed moderate-to-excellent resistance to washing, rubbing, and perspiration, as well as fastness to sublimation and light. In addition, the targeted printed samples were screened for their in vitro antibacterial activity against both Gram-positive and Gram-negative bacterial species. The azo compound
8a
showed the best antibacterial activity against
S. aureus
with inhibition zone of 23 mm which is higher than the reference drug Ampicillin (21 mm).</description><subject>Ampicillin</subject><subject>Analytical Chemistry</subject><subject>Azo compounds</subject><subject>Biochemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chromophores</subject><subject>Dispersion</subject><subject>Dyes</subject><subject>Inorganic Chemistry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Pastes</subject><subject>Perspiration</subject><subject>Physical Chemistry</subject><subject>Quinoline</subject><subject>Rubbing</subject><subject>Silk</subject><subject>Sublimation</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLxDAUhYsoOD7-gKuA62heTdulDL5gwIUK7kKa3kwzzCSdpEOpv96Oo7hzcTl3cc653C_Lrii5oYQUt4nygpeYMDoNqwQejrIZLXiOmWDl8e9Oio_T7CylFSF5QXIxy4bX0fctJJeQ9g3SXbd2Rvcu-ISCRSlsAHkYkHd9DEvw2ATfa-edX6IWeojBjGaKIP0ZcONSBzEBakZIqAYd97btzvmwdh6QaWPYhK4NES6yE6vXCS5_9Dx7f7h_mz_hxcvj8_xugQ2nVY-pzJumklKa0gpWENoYSSpbC6hobqXmFSMlCFvanDaCiqYWtREW-CQlB8HPs-tDbxfDdgepV6uwi346qZiksiqplGxysYPLxJBSBKu66DY6jooStQesDoDVBFh9A1bDFOKHUOr2f0L8q_4n9QVPC4IK</recordid><startdate>2022</startdate><enddate>2022</enddate><creator>Hassan, Khalid Mahmoud</creator><creator>ElKhabiery, Shaban Abdel Sattar</creator><creator>ElHaddad, Ghada Mahmoud</creator><creator>Shokair, Sameha Hassan</creator><creator>ElSayed, Ibrahim ElTantawy</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-1227-7931</orcidid><orcidid>https://orcid.org/0000-0001-6334-4423</orcidid></search><sort><creationdate>2022</creationdate><title>Synthesis and applications of some new nitrogen-containing heterocyclic azo-disperse dyes bearing quinoline chromophore</title><author>Hassan, Khalid Mahmoud ; ElKhabiery, Shaban Abdel Sattar ; ElHaddad, Ghada Mahmoud ; Shokair, Sameha Hassan ; ElSayed, Ibrahim ElTantawy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-165dd9666c8f42701dc609fb4e915f6a39208e4f8f51d414db4bc4fe34bc83e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Ampicillin</topic><topic>Analytical Chemistry</topic><topic>Azo compounds</topic><topic>Biochemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chromophores</topic><topic>Dispersion</topic><topic>Dyes</topic><topic>Inorganic Chemistry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Pastes</topic><topic>Perspiration</topic><topic>Physical Chemistry</topic><topic>Quinoline</topic><topic>Rubbing</topic><topic>Silk</topic><topic>Sublimation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hassan, Khalid Mahmoud</creatorcontrib><creatorcontrib>ElKhabiery, Shaban Abdel Sattar</creatorcontrib><creatorcontrib>ElHaddad, Ghada Mahmoud</creatorcontrib><creatorcontrib>Shokair, Sameha Hassan</creatorcontrib><creatorcontrib>ElSayed, Ibrahim ElTantawy</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hassan, Khalid Mahmoud</au><au>ElKhabiery, Shaban Abdel Sattar</au><au>ElHaddad, Ghada Mahmoud</au><au>Shokair, Sameha Hassan</au><au>ElSayed, Ibrahim ElTantawy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and applications of some new nitrogen-containing heterocyclic azo-disperse dyes bearing quinoline chromophore</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2022</date><risdate>2022</risdate><volume>19</volume><issue>1</issue><spage>147</spage><epage>158</epage><pages>147-158</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>A set of five novel nitrogen-containing heterocyclic azo-disperse dyes
8 (a–d)
and
10
were synthesized by diazotization of 4-bisaminoquinolines
3
, followed by coupling either with rhodanine analogues
6
modified at C-5 position or α-naphthol
9
. The chemical structures of
8(a–d)
and
10
were proven by the FT-IR, NMR, and mass spectroscopic techniques. Moreover, utilization of these azo dyes in preparing pastes for printing polyester fabric by silk screen traditional printing was achieved. The color strength and fastness properties of the synthesized dyes were also examined and showed moderate-to-excellent resistance to washing, rubbing, and perspiration, as well as fastness to sublimation and light. In addition, the targeted printed samples were screened for their in vitro antibacterial activity against both Gram-positive and Gram-negative bacterial species. The azo compound
8a
showed the best antibacterial activity against
S. aureus
with inhibition zone of 23 mm which is higher than the reference drug Ampicillin (21 mm).</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-021-02294-w</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0003-1227-7931</orcidid><orcidid>https://orcid.org/0000-0001-6334-4423</orcidid></addata></record> |
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| issn | 1735-207X 1735-2428 |
| language | eng |
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| source | SpringerNature Journals |
| subjects | Ampicillin Analytical Chemistry Azo compounds Biochemistry Chemical synthesis Chemistry Chemistry and Materials Science Chromophores Dispersion Dyes Inorganic Chemistry NMR Nuclear magnetic resonance Organic Chemistry Original Paper Pastes Perspiration Physical Chemistry Quinoline Rubbing Silk Sublimation |
| title | Synthesis and applications of some new nitrogen-containing heterocyclic azo-disperse dyes bearing quinoline chromophore |
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