Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations
A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reacti...
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| creator | Ujan, Rabail Arshad, Nasima Perveen, Fouzia Channar, Pervaiz Ali Lal, Bhajan Hussain, Mumtaz Hussain, Zahid Saeed, Aamer Shehzadi, Syeda Aaliya |
| description | A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reaction. This compound was further explored for its selectivity and sensitivity toward mercury (Hg
2+
) ions detection. Quantum chemical DFT calculations were performed to examine the adsorption of Hg(OOCCH
3
)
2
on the surface of compound 7. The charge distributions before and after adsorption showed charge transfer from 7 to Hg(OOCCH
3
)
2
which indicated that 7 was sensitive to Hg(OOCCH
3
)
2
molecule for Hg
+2
detection. The lowing in energy gap (Δ
E
), higher electrical conductivity and increased density of states (DOS) after Hg(OOCCH
3
)
2
adsorption further depicted the potential of 7 as a chemical sensor for Hg
+2
sensing. The photophysical potential of compound (7) was examined by employing a range of cations (Ba
2+
, Ca
2+
, Co
2+
, Hg
2+
, K
+
, Mg
2+
, Mn
2+
, Na
+
, NH
4+
and Pd
2+
). A significant hyperchromic shift in compound 7 spectrum (UV/ and fluorescence) upon equimolar addition of Hg
2+
ions indicated that the triazole-based compound (7) has exhibited selective interaction with Hg
2+
ion in preference to other cations. The maximum chelation of compound (7) with Hg
2+
was observed at
p
H 5.1 (slightly acidic medium). The compound (7) capability to recognize Hg
2+
was observed even at 0.1 µM detectable limit, indicating greater sensitivity of 7 toward Hg
2+
. No significant effect of competitive metal ions on 7 – Hg
2+
complex further authenticated robust selectivity and sensitivity of 7 toward sensing Hg
2+
ions. Binding mechanism indicated the formation of 2:1 complex of 7 - Hg
2+
. DFT and spectral findings complimented each other and proving the promising chemosensor candidacy of the compound 7 for Hg
2+
ions.
Graphic abstract |
| doi_str_mv | 10.1007/s11696-021-01804-7 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2580707756</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2580707756</sourcerecordid><originalsourceid>FETCH-LOGICAL-c249t-b1d448b45fb8c221c9226661adccf3b6a40024add67207d1a0f60539369e2a003</originalsourceid><addsrcrecordid>eNp9kE9LAzEQxYMoWKtfwFPAo41O_mzS9SZFbaHgRc8hTbJl63azJtuinv3gpq3gzdPAzO-9eTyELincUAB1myiVpSTAKAE6BkHUERpQziUpQRXHaABcSiJ5wU7RWUorACGggAH6njnf9nVVW9PXocWhwga3YesbbJvavhHnY731DtMRG3HSx9p8hcZjk3Dyjbd9PuLpkl3jndr5Pq9CvMM2rLtNv_c0DTatw_6jy1br_C0v6nbrU18v90A6RyeVaZK_-J1D9Pr48DKZkvnz02xyPyeWibInC-qEGC9EUS3GljFqS8aklNQ4ayu-kEYAMGGck4qBctRAJaHgJZelZwaAD9HVwbeL4X2TA-hV2MQcMGlWjEGBUoXMFDtQNoaUoq90l3Ob-Kkp6F3b-tC2zm3rfdtaZRE_iFKG26WPf9b_qH4ANR-DOQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2580707756</pqid></control><display><type>article</type><title>Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations</title><source>Springer Nature</source><creator>Ujan, Rabail ; Arshad, Nasima ; Perveen, Fouzia ; Channar, Pervaiz Ali ; Lal, Bhajan ; Hussain, Mumtaz ; Hussain, Zahid ; Saeed, Aamer ; Shehzadi, Syeda Aaliya</creator><creatorcontrib>Ujan, Rabail ; Arshad, Nasima ; Perveen, Fouzia ; Channar, Pervaiz Ali ; Lal, Bhajan ; Hussain, Mumtaz ; Hussain, Zahid ; Saeed, Aamer ; Shehzadi, Syeda Aaliya</creatorcontrib><description>A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reaction. This compound was further explored for its selectivity and sensitivity toward mercury (Hg
2+
) ions detection. Quantum chemical DFT calculations were performed to examine the adsorption of Hg(OOCCH
3
)
2
on the surface of compound 7. The charge distributions before and after adsorption showed charge transfer from 7 to Hg(OOCCH
3
)
2
which indicated that 7 was sensitive to Hg(OOCCH
3
)
2
molecule for Hg
+2
detection. The lowing in energy gap (Δ
E
), higher electrical conductivity and increased density of states (DOS) after Hg(OOCCH
3
)
2
adsorption further depicted the potential of 7 as a chemical sensor for Hg
+2
sensing. The photophysical potential of compound (7) was examined by employing a range of cations (Ba
2+
, Ca
2+
, Co
2+
, Hg
2+
, K
+
, Mg
2+
, Mn
2+
, Na
+
, NH
4+
and Pd
2+
). A significant hyperchromic shift in compound 7 spectrum (UV/ and fluorescence) upon equimolar addition of Hg
2+
ions indicated that the triazole-based compound (7) has exhibited selective interaction with Hg
2+
ion in preference to other cations. The maximum chelation of compound (7) with Hg
2+
was observed at
p
H 5.1 (slightly acidic medium). The compound (7) capability to recognize Hg
2+
was observed even at 0.1 µM detectable limit, indicating greater sensitivity of 7 toward Hg
2+
. No significant effect of competitive metal ions on 7 – Hg
2+
complex further authenticated robust selectivity and sensitivity of 7 toward sensing Hg
2+
ions. Binding mechanism indicated the formation of 2:1 complex of 7 - Hg
2+
. DFT and spectral findings complimented each other and proving the promising chemosensor candidacy of the compound 7 for Hg
2+
ions.
Graphic abstract</description><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>EISSN: 2585-7290</identifier><identifier>DOI: 10.1007/s11696-021-01804-7</identifier><language>eng</language><publisher>Warsaw: Versita</publisher><subject>Adsorption ; Biochemistry ; Biotechnology ; Calcium ions ; Cations ; Charge transfer ; Chelation ; Chemical sensors ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Chemoreceptors ; Cobalt ; Cycloaddition ; Density of states ; Electrical resistivity ; Energy gap ; Fluorescence ; Industrial Chemistry/Chemical Engineering ; Ion detectors ; Materials Science ; Medicinal Chemistry ; Mercury (metal) ; Original Paper ; Quantum chemistry ; Selectivity ; Sensitivity ; Triazoles</subject><ispartof>Chemical papers, 2021-12, Vol.75 (12), p.6377-6388</ispartof><rights>Institute of Chemistry, Slovak Academy of Sciences 2021</rights><rights>Institute of Chemistry, Slovak Academy of Sciences 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c249t-b1d448b45fb8c221c9226661adccf3b6a40024add67207d1a0f60539369e2a003</citedby><cites>FETCH-LOGICAL-c249t-b1d448b45fb8c221c9226661adccf3b6a40024add67207d1a0f60539369e2a003</cites><orcidid>0000-0002-4257-9909</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/s11696-021-01804-7$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11696-021-01804-7$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Ujan, Rabail</creatorcontrib><creatorcontrib>Arshad, Nasima</creatorcontrib><creatorcontrib>Perveen, Fouzia</creatorcontrib><creatorcontrib>Channar, Pervaiz Ali</creatorcontrib><creatorcontrib>Lal, Bhajan</creatorcontrib><creatorcontrib>Hussain, Mumtaz</creatorcontrib><creatorcontrib>Hussain, Zahid</creatorcontrib><creatorcontrib>Saeed, Aamer</creatorcontrib><creatorcontrib>Shehzadi, Syeda Aaliya</creatorcontrib><title>Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reaction. This compound was further explored for its selectivity and sensitivity toward mercury (Hg
2+
) ions detection. Quantum chemical DFT calculations were performed to examine the adsorption of Hg(OOCCH
3
)
2
on the surface of compound 7. The charge distributions before and after adsorption showed charge transfer from 7 to Hg(OOCCH
3
)
2
which indicated that 7 was sensitive to Hg(OOCCH
3
)
2
molecule for Hg
+2
detection. The lowing in energy gap (Δ
E
), higher electrical conductivity and increased density of states (DOS) after Hg(OOCCH
3
)
2
adsorption further depicted the potential of 7 as a chemical sensor for Hg
+2
sensing. The photophysical potential of compound (7) was examined by employing a range of cations (Ba
2+
, Ca
2+
, Co
2+
, Hg
2+
, K
+
, Mg
2+
, Mn
2+
, Na
+
, NH
4+
and Pd
2+
). A significant hyperchromic shift in compound 7 spectrum (UV/ and fluorescence) upon equimolar addition of Hg
2+
ions indicated that the triazole-based compound (7) has exhibited selective interaction with Hg
2+
ion in preference to other cations. The maximum chelation of compound (7) with Hg
2+
was observed at
p
H 5.1 (slightly acidic medium). The compound (7) capability to recognize Hg
2+
was observed even at 0.1 µM detectable limit, indicating greater sensitivity of 7 toward Hg
2+
. No significant effect of competitive metal ions on 7 – Hg
2+
complex further authenticated robust selectivity and sensitivity of 7 toward sensing Hg
2+
ions. Binding mechanism indicated the formation of 2:1 complex of 7 - Hg
2+
. DFT and spectral findings complimented each other and proving the promising chemosensor candidacy of the compound 7 for Hg
2+
ions.
Graphic abstract</description><subject>Adsorption</subject><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Calcium ions</subject><subject>Cations</subject><subject>Charge transfer</subject><subject>Chelation</subject><subject>Chemical sensors</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Chemoreceptors</subject><subject>Cobalt</subject><subject>Cycloaddition</subject><subject>Density of states</subject><subject>Electrical resistivity</subject><subject>Energy gap</subject><subject>Fluorescence</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Ion detectors</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>Mercury (metal)</subject><subject>Original Paper</subject><subject>Quantum chemistry</subject><subject>Selectivity</subject><subject>Sensitivity</subject><subject>Triazoles</subject><issn>0366-6352</issn><issn>1336-9075</issn><issn>2585-7290</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LAzEQxYMoWKtfwFPAo41O_mzS9SZFbaHgRc8hTbJl63azJtuinv3gpq3gzdPAzO-9eTyELincUAB1myiVpSTAKAE6BkHUERpQziUpQRXHaABcSiJ5wU7RWUorACGggAH6njnf9nVVW9PXocWhwga3YesbbJvavhHnY731DtMRG3HSx9p8hcZjk3Dyjbd9PuLpkl3jndr5Pq9CvMM2rLtNv_c0DTatw_6jy1br_C0v6nbrU18v90A6RyeVaZK_-J1D9Pr48DKZkvnz02xyPyeWibInC-qEGC9EUS3GljFqS8aklNQ4ayu-kEYAMGGck4qBctRAJaHgJZelZwaAD9HVwbeL4X2TA-hV2MQcMGlWjEGBUoXMFDtQNoaUoq90l3Ob-Kkp6F3b-tC2zm3rfdtaZRE_iFKG26WPf9b_qH4ANR-DOQ</recordid><startdate>20211201</startdate><enddate>20211201</enddate><creator>Ujan, Rabail</creator><creator>Arshad, Nasima</creator><creator>Perveen, Fouzia</creator><creator>Channar, Pervaiz Ali</creator><creator>Lal, Bhajan</creator><creator>Hussain, Mumtaz</creator><creator>Hussain, Zahid</creator><creator>Saeed, Aamer</creator><creator>Shehzadi, Syeda Aaliya</creator><general>Versita</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-4257-9909</orcidid></search><sort><creationdate>20211201</creationdate><title>Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations</title><author>Ujan, Rabail ; Arshad, Nasima ; Perveen, Fouzia ; Channar, Pervaiz Ali ; Lal, Bhajan ; Hussain, Mumtaz ; Hussain, Zahid ; Saeed, Aamer ; Shehzadi, Syeda Aaliya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c249t-b1d448b45fb8c221c9226661adccf3b6a40024add67207d1a0f60539369e2a003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Adsorption</topic><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Calcium ions</topic><topic>Cations</topic><topic>Charge transfer</topic><topic>Chelation</topic><topic>Chemical sensors</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Chemoreceptors</topic><topic>Cobalt</topic><topic>Cycloaddition</topic><topic>Density of states</topic><topic>Electrical resistivity</topic><topic>Energy gap</topic><topic>Fluorescence</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Ion detectors</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>Mercury (metal)</topic><topic>Original Paper</topic><topic>Quantum chemistry</topic><topic>Selectivity</topic><topic>Sensitivity</topic><topic>Triazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ujan, Rabail</creatorcontrib><creatorcontrib>Arshad, Nasima</creatorcontrib><creatorcontrib>Perveen, Fouzia</creatorcontrib><creatorcontrib>Channar, Pervaiz Ali</creatorcontrib><creatorcontrib>Lal, Bhajan</creatorcontrib><creatorcontrib>Hussain, Mumtaz</creatorcontrib><creatorcontrib>Hussain, Zahid</creatorcontrib><creatorcontrib>Saeed, Aamer</creatorcontrib><creatorcontrib>Shehzadi, Syeda Aaliya</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ujan, Rabail</au><au>Arshad, Nasima</au><au>Perveen, Fouzia</au><au>Channar, Pervaiz Ali</au><au>Lal, Bhajan</au><au>Hussain, Mumtaz</au><au>Hussain, Zahid</au><au>Saeed, Aamer</au><au>Shehzadi, Syeda Aaliya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2021-12-01</date><risdate>2021</risdate><volume>75</volume><issue>12</issue><spage>6377</spage><epage>6388</epage><pages>6377-6388</pages><issn>0366-6352</issn><eissn>1336-9075</eissn><eissn>2585-7290</eissn><abstract>A new triazole-substituted compound (7), namely {5-((2-methyl-4-(3-methyl-4-(prop-2-ynyloxy) benzyl) phenoxy) methyl)-1-(3-(nitrophenoxy) propyl)-1h-1, 2, 3-triazole}, was synthesized through the coupling of azido and propargylated precursors via click approach using 1,3-dipolar cycloaddition reaction. This compound was further explored for its selectivity and sensitivity toward mercury (Hg
2+
) ions detection. Quantum chemical DFT calculations were performed to examine the adsorption of Hg(OOCCH
3
)
2
on the surface of compound 7. The charge distributions before and after adsorption showed charge transfer from 7 to Hg(OOCCH
3
)
2
which indicated that 7 was sensitive to Hg(OOCCH
3
)
2
molecule for Hg
+2
detection. The lowing in energy gap (Δ
E
), higher electrical conductivity and increased density of states (DOS) after Hg(OOCCH
3
)
2
adsorption further depicted the potential of 7 as a chemical sensor for Hg
+2
sensing. The photophysical potential of compound (7) was examined by employing a range of cations (Ba
2+
, Ca
2+
, Co
2+
, Hg
2+
, K
+
, Mg
2+
, Mn
2+
, Na
+
, NH
4+
and Pd
2+
). A significant hyperchromic shift in compound 7 spectrum (UV/ and fluorescence) upon equimolar addition of Hg
2+
ions indicated that the triazole-based compound (7) has exhibited selective interaction with Hg
2+
ion in preference to other cations. The maximum chelation of compound (7) with Hg
2+
was observed at
p
H 5.1 (slightly acidic medium). The compound (7) capability to recognize Hg
2+
was observed even at 0.1 µM detectable limit, indicating greater sensitivity of 7 toward Hg
2+
. No significant effect of competitive metal ions on 7 – Hg
2+
complex further authenticated robust selectivity and sensitivity of 7 toward sensing Hg
2+
ions. Binding mechanism indicated the formation of 2:1 complex of 7 - Hg
2+
. DFT and spectral findings complimented each other and proving the promising chemosensor candidacy of the compound 7 for Hg
2+
ions.
Graphic abstract</abstract><cop>Warsaw</cop><pub>Versita</pub><doi>10.1007/s11696-021-01804-7</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-4257-9909</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0366-6352 |
| ispartof | Chemical papers, 2021-12, Vol.75 (12), p.6377-6388 |
| issn | 0366-6352 1336-9075 2585-7290 |
| language | eng |
| recordid | cdi_proquest_journals_2580707756 |
| source | Springer Nature |
| subjects | Adsorption Biochemistry Biotechnology Calcium ions Cations Charge transfer Chelation Chemical sensors Chemistry Chemistry and Materials Science Chemistry/Food Science Chemoreceptors Cobalt Cycloaddition Density of states Electrical resistivity Energy gap Fluorescence Industrial Chemistry/Chemical Engineering Ion detectors Materials Science Medicinal Chemistry Mercury (metal) Original Paper Quantum chemistry Selectivity Sensitivity Triazoles |
| title | Identification of a novel click-derived 1,2,3-triazole as selective Hg2+ ion detector: computational and experimental investigations |
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