Facile synthesis and exploration of excited state assisted two-photon absorption properties of D-A-D type thiophene-pyridine derivatives
A series of trigonal-shaped molecules ( TPyT and TPyP ) and a polymer ( P2TPy ) with donor-acceptor-donor (D-A-D) structural arrangement were designed with thiophene and 2,4,6-trisubstituted pyridine as the backbone i.e. , a 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine core structure, for th...
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| Veröffentlicht in: | Photochemical & photobiological sciences 2020-05, Vol.19 (5), p.726-736 |
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| creator | Kakekochi, Viprabha Chatnahalli Gangadharappa, Sathish Keloth, Chandrasekharan Wolcan, Ezequiel D, Udaya Kumar |
| description | A series of trigonal-shaped molecules (
TPyT
and
TPyP
) and a polymer (
P2TPy
) with donor-acceptor-donor (D-A-D) structural arrangement were designed with thiophene and 2,4,6-trisubstituted pyridine as the backbone
i.e.
, a 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine core structure, for the first time and synthesized
via
a microwave assisted one pot reaction. The extension of conjugation of the system by substituting thiophene acrylonitrile (
TPyT
) and phenyl acrylonitriles (
TPyP
and
P2TPy
)
via
low cost condensation reactions improved the linear optical, electronic and thermal properties of the synthesized compounds. Furthermore, the nonlinear absorption (NLA) was also enriched appreciably by increasing the conjugation. The three compounds showed an "effective two-photon absorption" phenomenon with the NLA coefficient (
β
eff
) of the order of 10
−10
m W
−1
. The suitability to be utilized in the fabrication of all-optical limiting devices is best achieved by polymer
P2TPy
as it exhibits substantially higher
β
eff
(7.02 × 10
−10
m W
−1
) and an extremely low optical limiting threshold (1.42 J cm
−2
).
Diagrammatic representation of excited state assisted two-photon absorption (2PA) behavior of a donor-acceptor type conjugated polymer (
P2TPy
) exhibiting an extremely low optical limiting threshold. |
| doi_str_mv | 10.1039/d0pp00047g |
| format | Article |
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TPyT
and
TPyP
) and a polymer (
P2TPy
) with donor-acceptor-donor (D-A-D) structural arrangement were designed with thiophene and 2,4,6-trisubstituted pyridine as the backbone
i.e.
, a 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine core structure, for the first time and synthesized
via
a microwave assisted one pot reaction. The extension of conjugation of the system by substituting thiophene acrylonitrile (
TPyT
) and phenyl acrylonitriles (
TPyP
and
P2TPy
)
via
low cost condensation reactions improved the linear optical, electronic and thermal properties of the synthesized compounds. Furthermore, the nonlinear absorption (NLA) was also enriched appreciably by increasing the conjugation. The three compounds showed an "effective two-photon absorption" phenomenon with the NLA coefficient (
β
eff
) of the order of 10
−10
m W
−1
. The suitability to be utilized in the fabrication of all-optical limiting devices is best achieved by polymer
P2TPy
as it exhibits substantially higher
β
eff
(7.02 × 10
−10
m W
−1
) and an extremely low optical limiting threshold (1.42 J cm
−2
).
Diagrammatic representation of excited state assisted two-photon absorption (2PA) behavior of a donor-acceptor type conjugated polymer (
P2TPy
) exhibiting an extremely low optical limiting threshold.</description><identifier>ISSN: 1474-905X</identifier><identifier>EISSN: 1474-9092</identifier><identifier>DOI: 10.1039/d0pp00047g</identifier><identifier>PMID: 32347874</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Absorption ; Acrylonitrile ; Acrylonitriles ; Biochemistry ; Biomaterials ; Chemistry ; Conjugation ; Constraining ; Fabrication ; Optical properties ; Photon absorption ; Photons ; Physical Chemistry ; Plant Sciences ; Polymers ; Pyridines ; Thermal properties ; Thermodynamic properties</subject><ispartof>Photochemical & photobiological sciences, 2020-05, Vol.19 (5), p.726-736</ispartof><rights>The Royal Society of Chemistry and Owner Societies 2020</rights><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c472t-c891c4982da268a7eef9ca49ea88944e40ab578f8a8727cc39ddce9e0686437c3</citedby><cites>FETCH-LOGICAL-c472t-c891c4982da268a7eef9ca49ea88944e40ab578f8a8727cc39ddce9e0686437c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1039/d0pp00047g$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1039/d0pp00047g$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32347874$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kakekochi, Viprabha</creatorcontrib><creatorcontrib>Chatnahalli Gangadharappa, Sathish</creatorcontrib><creatorcontrib>Keloth, Chandrasekharan</creatorcontrib><creatorcontrib>Wolcan, Ezequiel</creatorcontrib><creatorcontrib>D, Udaya Kumar</creatorcontrib><title>Facile synthesis and exploration of excited state assisted two-photon absorption properties of D-A-D type thiophene-pyridine derivatives</title><title>Photochemical & photobiological sciences</title><addtitle>Photochem Photobiol Sci</addtitle><addtitle>Photochem Photobiol Sci</addtitle><description>A series of trigonal-shaped molecules (
TPyT
and
TPyP
) and a polymer (
P2TPy
) with donor-acceptor-donor (D-A-D) structural arrangement were designed with thiophene and 2,4,6-trisubstituted pyridine as the backbone
i.e.
, a 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine core structure, for the first time and synthesized
via
a microwave assisted one pot reaction. The extension of conjugation of the system by substituting thiophene acrylonitrile (
TPyT
) and phenyl acrylonitriles (
TPyP
and
P2TPy
)
via
low cost condensation reactions improved the linear optical, electronic and thermal properties of the synthesized compounds. Furthermore, the nonlinear absorption (NLA) was also enriched appreciably by increasing the conjugation. The three compounds showed an "effective two-photon absorption" phenomenon with the NLA coefficient (
β
eff
) of the order of 10
−10
m W
−1
. The suitability to be utilized in the fabrication of all-optical limiting devices is best achieved by polymer
P2TPy
as it exhibits substantially higher
β
eff
(7.02 × 10
−10
m W
−1
) and an extremely low optical limiting threshold (1.42 J cm
−2
).
Diagrammatic representation of excited state assisted two-photon absorption (2PA) behavior of a donor-acceptor type conjugated polymer (
P2TPy
) exhibiting an extremely low optical limiting threshold.</description><subject>Absorption</subject><subject>Acrylonitrile</subject><subject>Acrylonitriles</subject><subject>Biochemistry</subject><subject>Biomaterials</subject><subject>Chemistry</subject><subject>Conjugation</subject><subject>Constraining</subject><subject>Fabrication</subject><subject>Optical properties</subject><subject>Photon absorption</subject><subject>Photons</subject><subject>Physical Chemistry</subject><subject>Plant Sciences</subject><subject>Polymers</subject><subject>Pyridines</subject><subject>Thermal properties</subject><subject>Thermodynamic properties</subject><issn>1474-905X</issn><issn>1474-9092</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90UFvVCEQAGBibGytXrxraLwYm6c8YB9wbFprmzTxoom3FxbmdWnePpBhq_sP_Nmybt1NjPEEk_mYmTCEvGjZu5YJ896zlBhjUt0-IketVLIxzPDHu_vs6yF5injHWDuTnXpCDgUXUmklj8jPS-vCCBTXU1kABqR28hR-pDFmW0KcaBxq6EIBT7HYAtRiZZuwfI9NWsRSkZ1jzOm3TzkmyCUAbp5eNGfNBS3rBLQsQkwLmKBJ6xx8mIB6yOG-trkHfEYOBjsiPH84j8mXyw-fz6-am08fr8_PbhonFS-N06Z10mjuLe-0VQCDcVYasFobKUEyO58pPWirFVfOCeO9AwOs050Uyolj8mZbt875bQVY-mVAB-NoJ4gr7Lkwnah_OWsrff0XvYurPNXpei5ZBVJwWdXbrXI5ImYY-pTD0uZ137J-s59-v5-KXz2UXM2X4Hf0z0IqON0CrKnpFvK-5z_LnWx1Rrertc_3yQ_VvPyfEb8Abu-xwA</recordid><startdate>20200520</startdate><enddate>20200520</enddate><creator>Kakekochi, Viprabha</creator><creator>Chatnahalli Gangadharappa, Sathish</creator><creator>Keloth, Chandrasekharan</creator><creator>Wolcan, Ezequiel</creator><creator>D, Udaya Kumar</creator><general>Springer International Publishing</general><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20200520</creationdate><title>Facile synthesis and exploration of excited state assisted two-photon absorption properties of D-A-D type thiophene-pyridine derivatives</title><author>Kakekochi, Viprabha ; Chatnahalli Gangadharappa, Sathish ; ; Keloth, Chandrasekharan ; Wolcan, Ezequiel ; D, Udaya Kumar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c472t-c891c4982da268a7eef9ca49ea88944e40ab578f8a8727cc39ddce9e0686437c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Absorption</topic><topic>Acrylonitrile</topic><topic>Acrylonitriles</topic><topic>Biochemistry</topic><topic>Biomaterials</topic><topic>Chemistry</topic><topic>Conjugation</topic><topic>Constraining</topic><topic>Fabrication</topic><topic>Optical properties</topic><topic>Photon absorption</topic><topic>Photons</topic><topic>Physical Chemistry</topic><topic>Plant Sciences</topic><topic>Polymers</topic><topic>Pyridines</topic><topic>Thermal properties</topic><topic>Thermodynamic properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kakekochi, Viprabha</creatorcontrib><creatorcontrib>Chatnahalli Gangadharappa, Sathish</creatorcontrib><creatorcontrib>Keloth, Chandrasekharan</creatorcontrib><creatorcontrib>Wolcan, Ezequiel</creatorcontrib><creatorcontrib>D, Udaya Kumar</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Photochemical & photobiological sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kakekochi, Viprabha</au><au>Chatnahalli Gangadharappa, Sathish</au><au>Keloth, Chandrasekharan</au><au>Wolcan, Ezequiel</au><au>D, Udaya Kumar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile synthesis and exploration of excited state assisted two-photon absorption properties of D-A-D type thiophene-pyridine derivatives</atitle><jtitle>Photochemical & photobiological sciences</jtitle><stitle>Photochem Photobiol Sci</stitle><addtitle>Photochem Photobiol Sci</addtitle><date>2020-05-20</date><risdate>2020</risdate><volume>19</volume><issue>5</issue><spage>726</spage><epage>736</epage><pages>726-736</pages><issn>1474-905X</issn><eissn>1474-9092</eissn><abstract>A series of trigonal-shaped molecules (
TPyT
and
TPyP
) and a polymer (
P2TPy
) with donor-acceptor-donor (D-A-D) structural arrangement were designed with thiophene and 2,4,6-trisubstituted pyridine as the backbone
i.e.
, a 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine core structure, for the first time and synthesized
via
a microwave assisted one pot reaction. The extension of conjugation of the system by substituting thiophene acrylonitrile (
TPyT
) and phenyl acrylonitriles (
TPyP
and
P2TPy
)
via
low cost condensation reactions improved the linear optical, electronic and thermal properties of the synthesized compounds. Furthermore, the nonlinear absorption (NLA) was also enriched appreciably by increasing the conjugation. The three compounds showed an "effective two-photon absorption" phenomenon with the NLA coefficient (
β
eff
) of the order of 10
−10
m W
−1
. The suitability to be utilized in the fabrication of all-optical limiting devices is best achieved by polymer
P2TPy
as it exhibits substantially higher
β
eff
(7.02 × 10
−10
m W
−1
) and an extremely low optical limiting threshold (1.42 J cm
−2
).
Diagrammatic representation of excited state assisted two-photon absorption (2PA) behavior of a donor-acceptor type conjugated polymer (
P2TPy
) exhibiting an extremely low optical limiting threshold.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>32347874</pmid><doi>10.1039/d0pp00047g</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| issn | 1474-905X 1474-9092 |
| language | eng |
| recordid | cdi_proquest_journals_2405134324 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Absorption Acrylonitrile Acrylonitriles Biochemistry Biomaterials Chemistry Conjugation Constraining Fabrication Optical properties Photon absorption Photons Physical Chemistry Plant Sciences Polymers Pyridines Thermal properties Thermodynamic properties |
| title | Facile synthesis and exploration of excited state assisted two-photon absorption properties of D-A-D type thiophene-pyridine derivatives |
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