Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines
In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the pres...
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| Veröffentlicht in: | New journal of chemistry 2021-06, Vol.45 (22), p.9912-9921 |
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| creator | Özdemir, Mücahit Artuç, Gamze Özgül Akkurt, Barbaros Yalç n, Bahattin Salan, Ümit Durmu, Mahmut Bulut, Mustafa |
| description | In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the presence of zinc acetate to yield 2,9(10),16(17),23(24)-tetrakis[2-phenoxy-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid] substituted zinc(
ii
) phthalocyanine. Some thiols, namely
n
-butanethiol (R
1
),
n
-hexanethiol (R
2
), 3-sulfanylpropionic acid (R
3
), and 7-sulfanyl-2
H
-1-benzopyran-2-one (R
4
), were reacted with this zinc(
ii
) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study.
Quinoline substituted zinc phthalocyanine derivatives were synthesized and characterized, and their photophysical and photochemical properties were investigated. |
| doi_str_mv | 10.1039/d1nj00854d |
| format | Article |
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ii
) phthalocyanine. Some thiols, namely
n
-butanethiol (R
1
),
n
-hexanethiol (R
2
), 3-sulfanylpropionic acid (R
3
), and 7-sulfanyl-2
H
-1-benzopyran-2-one (R
4
), were reacted with this zinc(
ii
) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study.
Quinoline substituted zinc phthalocyanine derivatives were synthesized and characterized, and their photophysical and photochemical properties were investigated.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj00854d</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetic acid ; Acids ; Fluorescence ; Photochemistry ; Photodynamic therapy ; Quinoline ; Singlet oxygen ; Substitution reactions ; Thiols ; Zinc acetate ; Zinc compounds</subject><ispartof>New journal of chemistry, 2021-06, Vol.45 (22), p.9912-9921</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-ee2506cbf1e23e79b640ef16ec066fc809c470ae7e925e121c7e46f7ab91a9393</citedby><cites>FETCH-LOGICAL-c281t-ee2506cbf1e23e79b640ef16ec066fc809c470ae7e925e121c7e46f7ab91a9393</cites><orcidid>0000-0003-0440-7345 ; 0000-0003-4448-1101 ; 0000-0002-0840-4953 ; 0000-0003-4066-3004</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Özdemir, Mücahit</creatorcontrib><creatorcontrib>Artuç, Gamze Özgül</creatorcontrib><creatorcontrib>Akkurt, Barbaros</creatorcontrib><creatorcontrib>Yalç n, Bahattin</creatorcontrib><creatorcontrib>Salan, Ümit</creatorcontrib><creatorcontrib>Durmu, Mahmut</creatorcontrib><creatorcontrib>Bulut, Mustafa</creatorcontrib><title>Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines</title><title>New journal of chemistry</title><description>In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the presence of zinc acetate to yield 2,9(10),16(17),23(24)-tetrakis[2-phenoxy-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid] substituted zinc(
ii
) phthalocyanine. Some thiols, namely
n
-butanethiol (R
1
),
n
-hexanethiol (R
2
), 3-sulfanylpropionic acid (R
3
), and 7-sulfanyl-2
H
-1-benzopyran-2-one (R
4
), were reacted with this zinc(
ii
) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study.
Quinoline substituted zinc phthalocyanine derivatives were synthesized and characterized, and their photophysical and photochemical properties were investigated.</description><subject>Acetic acid</subject><subject>Acids</subject><subject>Fluorescence</subject><subject>Photochemistry</subject><subject>Photodynamic therapy</subject><subject>Quinoline</subject><subject>Singlet oxygen</subject><subject>Substitution reactions</subject><subject>Thiols</subject><subject>Zinc acetate</subject><subject>Zinc compounds</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpN0U1LxDAQBuAiCurqxbtQ8OLKVjNtmm6O4rcselDPJU2nNFqTmqRg99f4U42uqJdMmHmYObxRtAfkGEjGT2rQz4TMc1qvRVuQMZ7wlMF6-AOlCckp24y2nQsGoGCwFX08jNq36JSbxbIVVkiPVi2FV0bP4r413vTt6JQMc6HrVUe2-Kqct2NsmrgPvm_Riq4bYzdUzis_eKxjj96KF-UO3walTaf02KFvw6MxeG3ex2ny3y-VlofTcMG3ojNyFFppdDvRRiM6h7s_dRI9XV48nl0ni_urm7PTRSLTOfgEMc0Jk1UDmGZY8IpRgg0wlISxRs4Jl7QgAgvkaY6QgiyQsqYQFQfBM55NooPV3t6atwGdL5_NYHU4WaZ5VjDKKORBHa2UtMY5i03ZW_Uq7FgCKb8SKM_h7vY7gfOA91fYOvnr_hLKPgEkPYlN</recordid><startdate>20210614</startdate><enddate>20210614</enddate><creator>Özdemir, Mücahit</creator><creator>Artuç, Gamze Özgül</creator><creator>Akkurt, Barbaros</creator><creator>Yalç n, Bahattin</creator><creator>Salan, Ümit</creator><creator>Durmu, Mahmut</creator><creator>Bulut, Mustafa</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/0000-0003-0440-7345</orcidid><orcidid>https://orcid.org/0000-0003-4448-1101</orcidid><orcidid>https://orcid.org/0000-0002-0840-4953</orcidid><orcidid>https://orcid.org/0000-0003-4066-3004</orcidid></search><sort><creationdate>20210614</creationdate><title>Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines</title><author>Özdemir, Mücahit ; Artuç, Gamze Özgül ; Akkurt, Barbaros ; Yalç n, Bahattin ; Salan, Ümit ; Durmu, Mahmut ; Bulut, Mustafa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-ee2506cbf1e23e79b640ef16ec066fc809c470ae7e925e121c7e46f7ab91a9393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acetic acid</topic><topic>Acids</topic><topic>Fluorescence</topic><topic>Photochemistry</topic><topic>Photodynamic therapy</topic><topic>Quinoline</topic><topic>Singlet oxygen</topic><topic>Substitution reactions</topic><topic>Thiols</topic><topic>Zinc acetate</topic><topic>Zinc compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Özdemir, Mücahit</creatorcontrib><creatorcontrib>Artuç, Gamze Özgül</creatorcontrib><creatorcontrib>Akkurt, Barbaros</creatorcontrib><creatorcontrib>Yalç n, Bahattin</creatorcontrib><creatorcontrib>Salan, Ümit</creatorcontrib><creatorcontrib>Durmu, Mahmut</creatorcontrib><creatorcontrib>Bulut, Mustafa</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>Özdemir, Mücahit</au><au>Artuç, Gamze Özgül</au><au>Akkurt, Barbaros</au><au>Yalç n, Bahattin</au><au>Salan, Ümit</au><au>Durmu, Mahmut</au><au>Bulut, Mustafa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines</atitle><jtitle>New journal of chemistry</jtitle><date>2021-06-14</date><risdate>2021</risdate><volume>45</volume><issue>22</issue><spage>9912</spage><epage>9921</epage><pages>9912-9921</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the presence of zinc acetate to yield 2,9(10),16(17),23(24)-tetrakis[2-phenoxy-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid] substituted zinc(
ii
) phthalocyanine. Some thiols, namely
n
-butanethiol (R
1
),
n
-hexanethiol (R
2
), 3-sulfanylpropionic acid (R
3
), and 7-sulfanyl-2
H
-1-benzopyran-2-one (R
4
), were reacted with this zinc(
ii
) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study.
Quinoline substituted zinc phthalocyanine derivatives were synthesized and characterized, and their photophysical and photochemical properties were investigated.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj00854d</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-0440-7345</orcidid><orcidid>https://orcid.org/0000-0003-4448-1101</orcidid><orcidid>https://orcid.org/0000-0002-0840-4953</orcidid><orcidid>https://orcid.org/0000-0003-4066-3004</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2021-06, Vol.45 (22), p.9912-9921 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D1NJ00854D |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetic acid Acids Fluorescence Photochemistry Photodynamic therapy Quinoline Singlet oxygen Substitution reactions Thiols Zinc acetate Zinc compounds |
| title | Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines |
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