Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions
A series of 1,4-phenylenes X-C(6)H(4)-BDB with a 1,3,2-benzodiazaborolyl (BDB) and a phosphorus based end group [X = PPh(2) (2), P(O)Ph(2) (3), P(S)Ph(2) (4), P(Se)Ph(2) (5), P(AuCl)Ph(2) (6) and P(Me)Ph(2) (7)] as well as 2-(2')thienyl-1,3,2-benzodiazaboroles with a second end group X [X = PPh...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2012-09, Vol.41 (34), p.10440-10452 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Weber, Lothar Kuhtz, Henry Böhling, Lena Brockhinke, Andreas Chrostowska, Anna Dargelos, Alain Mazière, Audrey Stammler, Hans-Georg Neumann, Beate |
| description | A series of 1,4-phenylenes X-C(6)H(4)-BDB with a 1,3,2-benzodiazaborolyl (BDB) and a phosphorus based end group [X = PPh(2) (2), P(O)Ph(2) (3), P(S)Ph(2) (4), P(Se)Ph(2) (5), P(AuCl)Ph(2) (6) and P(Me)Ph(2) (7)] as well as 2-(2')thienyl-1,3,2-benzodiazaboroles with a second end group X [X = PPh(2) (8), P(S)Ph(2) (9), P(Se)Ph(2) (10) and P(Me)Ph(2) (11)] in the 5' position were synthesised using established methodologies. Molecular structures of 2-9 and 11 were determined by X-ray diffraction. Compounds 3, 4, 6, 7, 9 and 11 show intense blue luminescence in cyclohexane, toluene, chloroform, dichloromethane and tetrahydrofuran with pronounced solvatochromism. Thereby Stokes shifts in the range of 8950-10,440 cm(-1) and quantum yields up to 0.70 were observed in dichloromethane solutions. In contrast to this, for the selenides 5 and 10 quantum yields are small ( |
| doi_str_mv | 10.1039/c2dt30666b |
| format | Article |
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Molecular structures of 2-9 and 11 were determined by X-ray diffraction. Compounds 3, 4, 6, 7, 9 and 11 show intense blue luminescence in cyclohexane, toluene, chloroform, dichloromethane and tetrahydrofuran with pronounced solvatochromism. Thereby Stokes shifts in the range of 8950-10,440 cm(-1) and quantum yields up to 0.70 were observed in dichloromethane solutions. In contrast to this, for the selenides 5 and 10 quantum yields are small (<0.1). The absorption maxima (298-340 nm) are well reproduced by TD-DFT computations (B3LYB/G-311G(d,p)) and arise from strong HOMO-LUMO transitions. With the exception of 5 and 10 the HOMOs of the molecules under study are mainly located on the benzodiazaborole group. In 5 and 10 the HOMOs are on the selenium atoms. The LUMOs of all new neutral molecules are mainly represented by the phenylene or thiophene bridge. In the phosphonium cations the LUMOs have additional contributions from the phosphonium unit.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c2dt30666b</identifier><identifier>PMID: 22797550</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Bridges (structures) ; Cations ; Chemical Sciences ; Dichloromethane ; Diffraction ; Fluid flow ; Inorganic chemistry ; Mathematical models ; Maxima ; Molecular structure ; Organic chemistry</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2012-09, Vol.41 (34), p.10440-10452</ispartof><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c387t-8d63e3c498298573656ed120defb2e3a2f0f9ff7e28b6bd2e9bab204783879203</citedby><cites>FETCH-LOGICAL-c387t-8d63e3c498298573656ed120defb2e3a2f0f9ff7e28b6bd2e9bab204783879203</cites><orcidid>0000-0003-0371-4546</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22797550$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01566330$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Weber, Lothar</creatorcontrib><creatorcontrib>Kuhtz, Henry</creatorcontrib><creatorcontrib>Böhling, Lena</creatorcontrib><creatorcontrib>Brockhinke, Andreas</creatorcontrib><creatorcontrib>Chrostowska, Anna</creatorcontrib><creatorcontrib>Dargelos, Alain</creatorcontrib><creatorcontrib>Mazière, Audrey</creatorcontrib><creatorcontrib>Stammler, Hans-Georg</creatorcontrib><creatorcontrib>Neumann, Beate</creatorcontrib><title>Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>A series of 1,4-phenylenes X-C(6)H(4)-BDB with a 1,3,2-benzodiazaborolyl (BDB) and a phosphorus based end group [X = PPh(2) (2), P(O)Ph(2) (3), P(S)Ph(2) (4), P(Se)Ph(2) (5), P(AuCl)Ph(2) (6) and P(Me)Ph(2) (7)] as well as 2-(2')thienyl-1,3,2-benzodiazaboroles with a second end group X [X = PPh(2) (8), P(S)Ph(2) (9), P(Se)Ph(2) (10) and P(Me)Ph(2) (11)] in the 5' position were synthesised using established methodologies. Molecular structures of 2-9 and 11 were determined by X-ray diffraction. Compounds 3, 4, 6, 7, 9 and 11 show intense blue luminescence in cyclohexane, toluene, chloroform, dichloromethane and tetrahydrofuran with pronounced solvatochromism. Thereby Stokes shifts in the range of 8950-10,440 cm(-1) and quantum yields up to 0.70 were observed in dichloromethane solutions. In contrast to this, for the selenides 5 and 10 quantum yields are small (<0.1). The absorption maxima (298-340 nm) are well reproduced by TD-DFT computations (B3LYB/G-311G(d,p)) and arise from strong HOMO-LUMO transitions. With the exception of 5 and 10 the HOMOs of the molecules under study are mainly located on the benzodiazaborole group. In 5 and 10 the HOMOs are on the selenium atoms. The LUMOs of all new neutral molecules are mainly represented by the phenylene or thiophene bridge. In the phosphonium cations the LUMOs have additional contributions from the phosphonium unit.</description><subject>Bridges (structures)</subject><subject>Cations</subject><subject>Chemical Sciences</subject><subject>Dichloromethane</subject><subject>Diffraction</subject><subject>Fluid flow</subject><subject>Inorganic chemistry</subject><subject>Mathematical models</subject><subject>Maxima</subject><subject>Molecular structure</subject><subject>Organic chemistry</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqNkU1v1DAQhi0Eou3ChR-AcoRqA_Z4Y8fHqgKKtFIPhXPkjzEJytrBTora_nlc7bIcqTSjGY2eeTUfhLxh9AOjXH204GZOhRDmGTllGylrBXzz_JiDOCFnOf-kFIA28JKcAEglm4aekoebuzD3mDFX0Vcpujr3ekJX-XGJCbPFMFdszddQGwz30Q36XpuY4lg6fg9zX019zMXDsOzWlQ7uUNABK9vr0cYfGAaHlbYWpzmmyi_BzkMM-RV54fWY8fUhrsj3z5--XV7V2-svXy8vtrXlrZzr1gmO3G5UC6ptJBeNQMeAOvQGkGvw1CvvJUJrhHGAymgDdCPb0q6A8hV5v9ct43RTGnY63XVRD93VxbZ7rFHWCME5vWWFfbdnpxR_LZjnbjeUI4xj2ScuuWOSU8aAF_svSlsAxph6girlnDWqLWFFzveoTTHnhP44MaOPnOr-vbvAbw-6i9mhO6J__8v_AFKopXs</recordid><startdate>20120914</startdate><enddate>20120914</enddate><creator>Weber, Lothar</creator><creator>Kuhtz, Henry</creator><creator>Böhling, Lena</creator><creator>Brockhinke, Andreas</creator><creator>Chrostowska, Anna</creator><creator>Dargelos, Alain</creator><creator>Mazière, Audrey</creator><creator>Stammler, Hans-Georg</creator><creator>Neumann, Beate</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7SR</scope><scope>8BQ</scope><scope>JG9</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-0371-4546</orcidid></search><sort><creationdate>20120914</creationdate><title>Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions</title><author>Weber, Lothar ; Kuhtz, Henry ; Böhling, Lena ; Brockhinke, Andreas ; Chrostowska, Anna ; Dargelos, Alain ; Mazière, Audrey ; Stammler, Hans-Georg ; Neumann, Beate</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-8d63e3c498298573656ed120defb2e3a2f0f9ff7e28b6bd2e9bab204783879203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Bridges (structures)</topic><topic>Cations</topic><topic>Chemical Sciences</topic><topic>Dichloromethane</topic><topic>Diffraction</topic><topic>Fluid flow</topic><topic>Inorganic chemistry</topic><topic>Mathematical models</topic><topic>Maxima</topic><topic>Molecular structure</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weber, Lothar</creatorcontrib><creatorcontrib>Kuhtz, Henry</creatorcontrib><creatorcontrib>Böhling, Lena</creatorcontrib><creatorcontrib>Brockhinke, Andreas</creatorcontrib><creatorcontrib>Chrostowska, Anna</creatorcontrib><creatorcontrib>Dargelos, Alain</creatorcontrib><creatorcontrib>Mazière, Audrey</creatorcontrib><creatorcontrib>Stammler, Hans-Georg</creatorcontrib><creatorcontrib>Neumann, Beate</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Materials Research Database</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weber, Lothar</au><au>Kuhtz, Henry</au><au>Böhling, Lena</au><au>Brockhinke, Andreas</au><au>Chrostowska, Anna</au><au>Dargelos, Alain</au><au>Mazière, Audrey</au><au>Stammler, Hans-Georg</au><au>Neumann, Beate</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2012-09-14</date><risdate>2012</risdate><volume>41</volume><issue>34</issue><spage>10440</spage><epage>10452</epage><pages>10440-10452</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A series of 1,4-phenylenes X-C(6)H(4)-BDB with a 1,3,2-benzodiazaborolyl (BDB) and a phosphorus based end group [X = PPh(2) (2), P(O)Ph(2) (3), P(S)Ph(2) (4), P(Se)Ph(2) (5), P(AuCl)Ph(2) (6) and P(Me)Ph(2) (7)] as well as 2-(2')thienyl-1,3,2-benzodiazaboroles with a second end group X [X = PPh(2) (8), P(S)Ph(2) (9), P(Se)Ph(2) (10) and P(Me)Ph(2) (11)] in the 5' position were synthesised using established methodologies. Molecular structures of 2-9 and 11 were determined by X-ray diffraction. Compounds 3, 4, 6, 7, 9 and 11 show intense blue luminescence in cyclohexane, toluene, chloroform, dichloromethane and tetrahydrofuran with pronounced solvatochromism. Thereby Stokes shifts in the range of 8950-10,440 cm(-1) and quantum yields up to 0.70 were observed in dichloromethane solutions. In contrast to this, for the selenides 5 and 10 quantum yields are small (<0.1). The absorption maxima (298-340 nm) are well reproduced by TD-DFT computations (B3LYB/G-311G(d,p)) and arise from strong HOMO-LUMO transitions. With the exception of 5 and 10 the HOMOs of the molecules under study are mainly located on the benzodiazaborole group. In 5 and 10 the HOMOs are on the selenium atoms. The LUMOs of all new neutral molecules are mainly represented by the phenylene or thiophene bridge. In the phosphonium cations the LUMOs have additional contributions from the phosphonium unit.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>22797550</pmid><doi>10.1039/c2dt30666b</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-0371-4546</orcidid></addata></record> |
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| subjects | Bridges (structures) Cations Chemical Sciences Dichloromethane Diffraction Fluid flow Inorganic chemistry Mathematical models Maxima Molecular structure Organic chemistry |
| title | Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions |
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