Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes
The synthesis and characterization of four new tetracyanobutadiene (TCBD) derivatives ( 1 , 3c and 4b-c ) incorporating tosylamido and 4-triphenylamino moieties are reported. Along with those of five closely related or differently branched TCBDs derivatives ( 2 , 3a-b , 4c and 5 ), their linear and...
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| Veröffentlicht in: | Physical chemistry chemical physics : PCCP 2021-10, Vol.23 (39), p.22283-22297 |
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| creator | Ripoche, Nicolas Betou, Marie Philippe, Clotilde Trolez, Yann Mongin, Olivier Dudek, Marta Pokladek, Ziemowit Matczyszyn, Katarzyna Samoc, Marek Sahnoune, Hiba Halet, Jean-François Roisnel, Thierry Toupet, Loic Cordier, Marie Moxey, Graeme J Humphrey, Mark G Paul, Frédéric |
| description | The synthesis and characterization of four new tetracyanobutadiene (TCBD) derivatives (
1
,
3c
and
4b-c
) incorporating tosylamido and 4-triphenylamino moieties are reported. Along with those of five closely related or differently branched TCBDs derivatives (
2
,
3a-b
,
4c
and
5
), their linear and (third-order) nonlinear optical properties were investigated by electronic absorption spectroscopy and Z-scan measurements. Among these compounds, the tri-branched compounds
3c
and
5
are the most active two-photon absorbers, with effective cross-sections of 275 and 350 GM at 900 nm, respectively. These properties are briefly discussed with the help of DFT calculations, focussing on structural and electronic factors, and contextualized with results obtained previously for related compounds.
The structural and electronic factors influencing their two-photon absorption cross-sections of nine TCBD derivatives are discussed. |
| doi_str_mv | 10.1039/d1cp03346h |
| format | Article |
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1
,
3c
and
4b-c
) incorporating tosylamido and 4-triphenylamino moieties are reported. Along with those of five closely related or differently branched TCBDs derivatives (
2
,
3a-b
,
4c
and
5
), their linear and (third-order) nonlinear optical properties were investigated by electronic absorption spectroscopy and Z-scan measurements. Among these compounds, the tri-branched compounds
3c
and
5
are the most active two-photon absorbers, with effective cross-sections of 275 and 350 GM at 900 nm, respectively. These properties are briefly discussed with the help of DFT calculations, focussing on structural and electronic factors, and contextualized with results obtained previously for related compounds.
The structural and electronic factors influencing their two-photon absorption cross-sections of nine TCBD derivatives are discussed.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/d1cp03346h</identifier><identifier>PMID: 34585692</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chemical Sciences ; Mathematical analysis ; Optical properties ; Photon absorption ; Photons ; Physics</subject><ispartof>Physical chemistry chemical physics : PCCP, 2021-10, Vol.23 (39), p.22283-22297</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><rights>Attribution - NonCommercial</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-179abd65fce63cafb3a311dc997e9bf1fe19eb48333db58930418e22a928bee93</citedby><cites>FETCH-LOGICAL-c384t-179abd65fce63cafb3a311dc997e9bf1fe19eb48333db58930418e22a928bee93</cites><orcidid>0000-0002-7743-9623 ; 0000-0002-8256-0129 ; 0000-0002-5421-9556 ; 0000-0002-5404-2455 ; 0000-0001-8578-8340 ; 0000-0003-0917-2725 ; 0000-0002-4433-6783 ; 0000-0001-6749-0903 ; 0000-0002-2315-4200 ; 0000-0002-8057-8579 ; 0000-0002-6088-4472</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,777,781,882,27905,27906</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03369351$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Ripoche, Nicolas</creatorcontrib><creatorcontrib>Betou, Marie</creatorcontrib><creatorcontrib>Philippe, Clotilde</creatorcontrib><creatorcontrib>Trolez, Yann</creatorcontrib><creatorcontrib>Mongin, Olivier</creatorcontrib><creatorcontrib>Dudek, Marta</creatorcontrib><creatorcontrib>Pokladek, Ziemowit</creatorcontrib><creatorcontrib>Matczyszyn, Katarzyna</creatorcontrib><creatorcontrib>Samoc, Marek</creatorcontrib><creatorcontrib>Sahnoune, Hiba</creatorcontrib><creatorcontrib>Halet, Jean-François</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Toupet, Loic</creatorcontrib><creatorcontrib>Cordier, Marie</creatorcontrib><creatorcontrib>Moxey, Graeme J</creatorcontrib><creatorcontrib>Humphrey, Mark G</creatorcontrib><creatorcontrib>Paul, Frédéric</creatorcontrib><title>Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes</title><title>Physical chemistry chemical physics : PCCP</title><description>The synthesis and characterization of four new tetracyanobutadiene (TCBD) derivatives (
1
,
3c
and
4b-c
) incorporating tosylamido and 4-triphenylamino moieties are reported. Along with those of five closely related or differently branched TCBDs derivatives (
2
,
3a-b
,
4c
and
5
), their linear and (third-order) nonlinear optical properties were investigated by electronic absorption spectroscopy and Z-scan measurements. Among these compounds, the tri-branched compounds
3c
and
5
are the most active two-photon absorbers, with effective cross-sections of 275 and 350 GM at 900 nm, respectively. These properties are briefly discussed with the help of DFT calculations, focussing on structural and electronic factors, and contextualized with results obtained previously for related compounds.
The structural and electronic factors influencing their two-photon absorption cross-sections of nine TCBD derivatives are discussed.</description><subject>Chemical Sciences</subject><subject>Mathematical analysis</subject><subject>Optical properties</subject><subject>Photon absorption</subject><subject>Photons</subject><subject>Physics</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkc1rGzEQxUVJqBO3l94DC7m0xdtodrQfOho3iQOG9pCeF612FiusVxtJm-D_vnJcXMhpHsOPmXnzGPsC_AdwlDct6JEjimL7gV2AKDCVvBJnJ10WM3bp_RPnHHLAj2yGIq_yQmYXTD--2nTc2mCHRDXeujGYKEdnR3LBkE9sl-ymPpjR9solwRnl9r3amcHeBOvfZGsTWMBCLEQaKDil92qwzRRUa2gg_4mdd6r39PlfnbM_d7ePq3W6-XX_sFpuUo2VCCmUUjVtkXeaCtSqa1AhQKulLEk2HXQEkhpRIWLb5JVELqCiLFMyqxoiiXP27Th3q_p6dGYXL62tMvV6uakPvfikQmIOLxDZr0c2On2eyId6Z7ymvlcD2cnXWV6WJWalxIhev0Of7OSG6CRSVfxoJvlh-fcjpZ313lF3ugB4fYip_gmr328xrSN8dYSd1yfuf4z4Fy38jW8</recordid><startdate>20211013</startdate><enddate>20211013</enddate><creator>Ripoche, Nicolas</creator><creator>Betou, Marie</creator><creator>Philippe, Clotilde</creator><creator>Trolez, Yann</creator><creator>Mongin, Olivier</creator><creator>Dudek, Marta</creator><creator>Pokladek, Ziemowit</creator><creator>Matczyszyn, Katarzyna</creator><creator>Samoc, Marek</creator><creator>Sahnoune, Hiba</creator><creator>Halet, Jean-François</creator><creator>Roisnel, Thierry</creator><creator>Toupet, Loic</creator><creator>Cordier, Marie</creator><creator>Moxey, Graeme J</creator><creator>Humphrey, Mark G</creator><creator>Paul, Frédéric</creator><general>Royal Society of Chemistry</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><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-7743-9623</orcidid><orcidid>https://orcid.org/0000-0002-8256-0129</orcidid><orcidid>https://orcid.org/0000-0002-5421-9556</orcidid><orcidid>https://orcid.org/0000-0002-5404-2455</orcidid><orcidid>https://orcid.org/0000-0001-8578-8340</orcidid><orcidid>https://orcid.org/0000-0003-0917-2725</orcidid><orcidid>https://orcid.org/0000-0002-4433-6783</orcidid><orcidid>https://orcid.org/0000-0001-6749-0903</orcidid><orcidid>https://orcid.org/0000-0002-2315-4200</orcidid><orcidid>https://orcid.org/0000-0002-8057-8579</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid></search><sort><creationdate>20211013</creationdate><title>Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes</title><author>Ripoche, Nicolas ; Betou, Marie ; Philippe, Clotilde ; Trolez, Yann ; Mongin, Olivier ; Dudek, Marta ; Pokladek, Ziemowit ; Matczyszyn, Katarzyna ; Samoc, Marek ; Sahnoune, Hiba ; Halet, Jean-François ; Roisnel, Thierry ; Toupet, Loic ; Cordier, Marie ; Moxey, Graeme J ; Humphrey, Mark G ; Paul, Frédéric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-179abd65fce63cafb3a311dc997e9bf1fe19eb48333db58930418e22a928bee93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemical Sciences</topic><topic>Mathematical analysis</topic><topic>Optical properties</topic><topic>Photon absorption</topic><topic>Photons</topic><topic>Physics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ripoche, Nicolas</creatorcontrib><creatorcontrib>Betou, Marie</creatorcontrib><creatorcontrib>Philippe, Clotilde</creatorcontrib><creatorcontrib>Trolez, Yann</creatorcontrib><creatorcontrib>Mongin, Olivier</creatorcontrib><creatorcontrib>Dudek, Marta</creatorcontrib><creatorcontrib>Pokladek, Ziemowit</creatorcontrib><creatorcontrib>Matczyszyn, Katarzyna</creatorcontrib><creatorcontrib>Samoc, Marek</creatorcontrib><creatorcontrib>Sahnoune, Hiba</creatorcontrib><creatorcontrib>Halet, Jean-François</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Toupet, Loic</creatorcontrib><creatorcontrib>Cordier, Marie</creatorcontrib><creatorcontrib>Moxey, Graeme J</creatorcontrib><creatorcontrib>Humphrey, Mark G</creatorcontrib><creatorcontrib>Paul, Frédéric</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><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ripoche, Nicolas</au><au>Betou, Marie</au><au>Philippe, Clotilde</au><au>Trolez, Yann</au><au>Mongin, Olivier</au><au>Dudek, Marta</au><au>Pokladek, Ziemowit</au><au>Matczyszyn, Katarzyna</au><au>Samoc, Marek</au><au>Sahnoune, Hiba</au><au>Halet, Jean-François</au><au>Roisnel, Thierry</au><au>Toupet, Loic</au><au>Cordier, Marie</au><au>Moxey, Graeme J</au><au>Humphrey, Mark G</au><au>Paul, Frédéric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><date>2021-10-13</date><risdate>2021</risdate><volume>23</volume><issue>39</issue><spage>22283</spage><epage>22297</epage><pages>22283-22297</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>The synthesis and characterization of four new tetracyanobutadiene (TCBD) derivatives (
1
,
3c
and
4b-c
) incorporating tosylamido and 4-triphenylamino moieties are reported. Along with those of five closely related or differently branched TCBDs derivatives (
2
,
3a-b
,
4c
and
5
), their linear and (third-order) nonlinear optical properties were investigated by electronic absorption spectroscopy and Z-scan measurements. Among these compounds, the tri-branched compounds
3c
and
5
are the most active two-photon absorbers, with effective cross-sections of 275 and 350 GM at 900 nm, respectively. These properties are briefly discussed with the help of DFT calculations, focussing on structural and electronic factors, and contextualized with results obtained previously for related compounds.
The structural and electronic factors influencing their two-photon absorption cross-sections of nine TCBD derivatives are discussed.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>34585692</pmid><doi>10.1039/d1cp03346h</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0002-7743-9623</orcidid><orcidid>https://orcid.org/0000-0002-8256-0129</orcidid><orcidid>https://orcid.org/0000-0002-5421-9556</orcidid><orcidid>https://orcid.org/0000-0002-5404-2455</orcidid><orcidid>https://orcid.org/0000-0001-8578-8340</orcidid><orcidid>https://orcid.org/0000-0003-0917-2725</orcidid><orcidid>https://orcid.org/0000-0002-4433-6783</orcidid><orcidid>https://orcid.org/0000-0001-6749-0903</orcidid><orcidid>https://orcid.org/0000-0002-2315-4200</orcidid><orcidid>https://orcid.org/0000-0002-8057-8579</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><oa>free_for_read</oa></addata></record> |
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| issn | 1463-9076 1463-9084 |
| language | eng |
| recordid | cdi_rsc_primary_d1cp03346h |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical Sciences Mathematical analysis Optical properties Photon absorption Photons Physics |
| title | Two-photon absorption properties of multipolar triarylamino/tosylamido 1,1,4,4-tetracyanobutadienes |
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