Challenging the Auxiliary Donor Effect on Molecular Hyperpolarizability in Thiophene-Containing Nonlinear Chromophores: X-ray Crystallographic and Optical Measurements on Two New Isomeric Chromophores
To reexamine the established “auxiliary donor” effect of thiophene in nonlinear optical (NLO) chromophores, we have prepared two isomeric donor−acceptor azo dyes, differing only in the position of the thiophene. Experimental analysis of these chromophores, including electric field-induced second har...
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| Veröffentlicht in: | Journal of organic chemistry 2004-11, Vol.69 (24), p.8239-8243 |
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| container_title | Journal of organic chemistry |
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| creator | Moylan, Christopher R McNelis, Brian J Nathan, Lawrence C Marques, Michael A Hermstad, Eric L Brichler, Benjamin A |
| description | To reexamine the established “auxiliary donor” effect of thiophene in nonlinear optical (NLO) chromophores, we have prepared two isomeric donor−acceptor azo dyes, differing only in the position of the thiophene. Experimental analysis of these chromophores, including electric field-induced second harmonic generation (EFISH) and X-ray crystallography, contradicts previous experimental findings on similar chromophores but is consistent with the majority of computational precedents. We have found that the thiophene on the donor side produces a compound with a larger dipole moment; however, the isomer with the thiophene on the acceptor side is more nonlinear and has a higher figure of merit for NLO device applications. |
| doi_str_mv | 10.1021/jo049230c |
| format | Article |
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Experimental analysis of these chromophores, including electric field-induced second harmonic generation (EFISH) and X-ray crystallography, contradicts previous experimental findings on similar chromophores but is consistent with the majority of computational precedents. We have found that the thiophene on the donor side produces a compound with a larger dipole moment; however, the isomer with the thiophene on the acceptor side is more nonlinear and has a higher figure of merit for NLO device applications.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo049230c</identifier><identifier>PMID: 15549793</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Azo Compounds - chemistry ; Chemical Phenomena ; Chemistry, Physical ; Coloring Agents - chemistry ; Condensed matter: electronic structure, electrical, magnetic, and optical properties ; Condensed matter: structure, mechanical and thermal properties ; Crystallography, X-Ray ; Electrooptical effects ; Exact sciences and technology ; Isomerism ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation ; Optical properties of bulk materials and thin films ; Organic compounds ; Physics ; Spectrophotometry, Infrared ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; Thiophenes - chemistry</subject><ispartof>Journal of organic chemistry, 2004-11, Vol.69 (24), p.8239-8243</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-32b8f542d5589b08a2eb269328d16b3493da1b1bbf62c3e0a469b378875383153</citedby><cites>FETCH-LOGICAL-a379t-32b8f542d5589b08a2eb269328d16b3493da1b1bbf62c3e0a469b378875383153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo049230c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo049230c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16308190$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15549793$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Moylan, Christopher R</creatorcontrib><creatorcontrib>McNelis, Brian J</creatorcontrib><creatorcontrib>Nathan, Lawrence C</creatorcontrib><creatorcontrib>Marques, Michael A</creatorcontrib><creatorcontrib>Hermstad, Eric L</creatorcontrib><creatorcontrib>Brichler, Benjamin A</creatorcontrib><title>Challenging the Auxiliary Donor Effect on Molecular Hyperpolarizability in Thiophene-Containing Nonlinear Chromophores: X-ray Crystallographic and Optical Measurements on Two New Isomeric Chromophores</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>To reexamine the established “auxiliary donor” effect of thiophene in nonlinear optical (NLO) chromophores, we have prepared two isomeric donor−acceptor azo dyes, differing only in the position of the thiophene. Experimental analysis of these chromophores, including electric field-induced second harmonic generation (EFISH) and X-ray crystallography, contradicts previous experimental findings on similar chromophores but is consistent with the majority of computational precedents. We have found that the thiophene on the donor side produces a compound with a larger dipole moment; however, the isomer with the thiophene on the acceptor side is more nonlinear and has a higher figure of merit for NLO device applications.</description><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Azo Compounds - chemistry</subject><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Coloring Agents - chemistry</subject><subject>Condensed matter: electronic structure, electrical, magnetic, and optical properties</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystallography, X-Ray</subject><subject>Electrooptical effects</subject><subject>Exact sciences and technology</subject><subject>Isomerism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation</subject><subject>Optical properties of bulk materials and thin films</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Spectrophotometry, Infrared</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>Thiophenes - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAUhSMEotPCghdA3oDEIuCfOInZVaF_UjsFOojZRXbmZuKS2MFO1IYVW56Nt-BJ8GhGHRZ4cy35u8dH50TRC4LfEkzJu1uLE0EZrh5FM8IpjlOBk8fRDGNKY0ZTdhAden-Lw-GcP40OCOeJyASbRb-LRrYtmLU2azQ0gI7He91q6Sb0wRrr0EldQzUga9CVbaEaW-nQ-dSD62246h9SBXyYkDZo0WjbN2AgLqwZpDYbzbk1rTYQtorG2S4A1oF__-fnL7SMnZxQ4SY_BA927WTf6ApJs0LX_aAr2aIrkH500IEZ_MbD4s6iOdyhC287cAH-V_RZ9KSWrYfnu3kUfTk9WRTn8eX12UVxfBlLlokhBKLymid0xXkuFM4lBUVTwWi-IqliiWArSRRRqk5pxQDLJBWKZXmecZYzwtlR9Hqr2zv7fQQ_lJ32FbStNGBHX6YZFoTlOIBvtmDlrPcO6rJ3ugvZlgSXm-bKh-YC-3InOqoOVntyV1UAXu0A6UM0tZOm0n7PpQznRGw-jbec9gPcP7xL9y0YYxkvFx9vypvl5-XX-ae0PN3rysoHP6MzIbv_GPwLE63BPg</recordid><startdate>20041126</startdate><enddate>20041126</enddate><creator>Moylan, Christopher R</creator><creator>McNelis, Brian J</creator><creator>Nathan, Lawrence C</creator><creator>Marques, Michael A</creator><creator>Hermstad, Eric L</creator><creator>Brichler, Benjamin A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20041126</creationdate><title>Challenging the Auxiliary Donor Effect on Molecular Hyperpolarizability in Thiophene-Containing Nonlinear Chromophores: X-ray Crystallographic and Optical Measurements on Two New Isomeric Chromophores</title><author>Moylan, Christopher R ; McNelis, Brian J ; Nathan, Lawrence C ; Marques, Michael A ; Hermstad, Eric L ; Brichler, Benjamin A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-32b8f542d5589b08a2eb269328d16b3493da1b1bbf62c3e0a469b378875383153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Azo Compounds - chemistry</topic><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Coloring Agents - chemistry</topic><topic>Condensed matter: electronic structure, electrical, magnetic, and optical properties</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystallography, X-Ray</topic><topic>Electrooptical effects</topic><topic>Exact sciences and technology</topic><topic>Isomerism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation</topic><topic>Optical properties of bulk materials and thin films</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Spectrophotometry, Infrared</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>Thiophenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moylan, Christopher R</creatorcontrib><creatorcontrib>McNelis, Brian J</creatorcontrib><creatorcontrib>Nathan, Lawrence C</creatorcontrib><creatorcontrib>Marques, Michael A</creatorcontrib><creatorcontrib>Hermstad, Eric L</creatorcontrib><creatorcontrib>Brichler, Benjamin A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moylan, Christopher R</au><au>McNelis, Brian J</au><au>Nathan, Lawrence C</au><au>Marques, Michael A</au><au>Hermstad, Eric L</au><au>Brichler, Benjamin A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Challenging the Auxiliary Donor Effect on Molecular Hyperpolarizability in Thiophene-Containing Nonlinear Chromophores: X-ray Crystallographic and Optical Measurements on Two New Isomeric Chromophores</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2004-11-26</date><risdate>2004</risdate><volume>69</volume><issue>24</issue><spage>8239</spage><epage>8243</epage><pages>8239-8243</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>To reexamine the established “auxiliary donor” effect of thiophene in nonlinear optical (NLO) chromophores, we have prepared two isomeric donor−acceptor azo dyes, differing only in the position of the thiophene. Experimental analysis of these chromophores, including electric field-induced second harmonic generation (EFISH) and X-ray crystallography, contradicts previous experimental findings on similar chromophores but is consistent with the majority of computational precedents. We have found that the thiophene on the donor side produces a compound with a larger dipole moment; however, the isomer with the thiophene on the acceptor side is more nonlinear and has a higher figure of merit for NLO device applications.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15549793</pmid><doi>10.1021/jo049230c</doi><tpages>5</tpages></addata></record> |
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| subjects | Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds Azo Compounds - chemistry Chemical Phenomena Chemistry, Physical Coloring Agents - chemistry Condensed matter: electronic structure, electrical, magnetic, and optical properties Condensed matter: structure, mechanical and thermal properties Crystallography, X-Ray Electrooptical effects Exact sciences and technology Isomerism Magnetic Resonance Spectroscopy Molecular Structure Optical properties and condensed-matter spectroscopy and other interactions of matter with particles and radiation Optical properties of bulk materials and thin films Organic compounds Physics Spectrophotometry, Infrared Structure of solids and liquids crystallography Structure of specific crystalline solids Thiophenes - chemistry |
| title | Challenging the Auxiliary Donor Effect on Molecular Hyperpolarizability in Thiophene-Containing Nonlinear Chromophores: X-ray Crystallographic and Optical Measurements on Two New Isomeric Chromophores |
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