Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a
A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starti...
Gespeichert in:
Hauptverfasser: | , , , , , , , |
---|---|
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 8733 |
---|---|
container_issue | 34 |
container_start_page | 8723 |
container_title | |
container_volume | 5 |
creator | Koldemir, Unsal Tinkham, Jonathan S Johnson, Robert Lim, Bogyu Yemam, Henok A Gagnon, Kevin J Parkin, Sean Sellinger, Alan |
description | A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.
Polycyclic aromatic hydrocarbon compounds based on 4,10 and 6,12-functionalized dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. |
doi_str_mv | 10.1039/c7tc02528a |
format | Article |
fullrecord | <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_c7tc02528a</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c7tc02528a</sourcerecordid><originalsourceid>FETCH-rsc_primary_c7tc02528a3</originalsourceid><addsrcrecordid>eNqFkM1LAzEQxaMoWGov4lUYbwpt3Y92u_W6bbGnHvQmUqbZbDeSzSxJVlj_etNW7EHQucwj82bejzB2FQbDMIinD3zieBCNoxRPWScKxsFgMo5HZz86Si5Yz9r3wFcaJmky7Zxcr4wraUsaFYz6YQCoc0j6YQS22VgnXeMkaaACcrkR-pNec1H0K01vvDStFVpATarlLVeSAxqq0HlhK1QKKlKCN0rYue_OkN5NmrpWohLaoWlB6oLMbsVn3M2fl_eAHygVbpQYQpbNMgg99jSa7LkOOh3Cggx49_6Rewzn02hrsC59Qo4O_WHIlgvwPnKlMCCOBIdEsELAbLV8hN_fd8nOC1RW9L57l90s5i_Z08BYvq6NrDz6-miPu-z2r_m6zov4vxtfsGSNFw</addsrcrecordid><sourcetype>Enrichment Source</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a</title><source>Royal Society Of Chemistry Journals</source><creator>Koldemir, Unsal ; Tinkham, Jonathan S ; Johnson, Robert ; Lim, Bogyu ; Yemam, Henok A ; Gagnon, Kevin J ; Parkin, Sean ; Sellinger, Alan</creator><creatorcontrib>Koldemir, Unsal ; Tinkham, Jonathan S ; Johnson, Robert ; Lim, Bogyu ; Yemam, Henok A ; Gagnon, Kevin J ; Parkin, Sean ; Sellinger, Alan</creatorcontrib><description>A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.
Polycyclic aromatic hydrocarbon compounds based on 4,10 and 6,12-functionalized dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture.</description><identifier>ISSN: 2050-7526</identifier><identifier>EISSN: 2050-7534</identifier><identifier>DOI: 10.1039/c7tc02528a</identifier><language>eng</language><creationdate>2017-08</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Koldemir, Unsal</creatorcontrib><creatorcontrib>Tinkham, Jonathan S</creatorcontrib><creatorcontrib>Johnson, Robert</creatorcontrib><creatorcontrib>Lim, Bogyu</creatorcontrib><creatorcontrib>Yemam, Henok A</creatorcontrib><creatorcontrib>Gagnon, Kevin J</creatorcontrib><creatorcontrib>Parkin, Sean</creatorcontrib><creatorcontrib>Sellinger, Alan</creatorcontrib><title>Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a</title><description>A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.
Polycyclic aromatic hydrocarbon compounds based on 4,10 and 6,12-functionalized dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture.</description><issn>2050-7526</issn><issn>2050-7534</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkM1LAzEQxaMoWGov4lUYbwpt3Y92u_W6bbGnHvQmUqbZbDeSzSxJVlj_etNW7EHQucwj82bejzB2FQbDMIinD3zieBCNoxRPWScKxsFgMo5HZz86Si5Yz9r3wFcaJmky7Zxcr4wraUsaFYz6YQCoc0j6YQS22VgnXeMkaaACcrkR-pNec1H0K01vvDStFVpATarlLVeSAxqq0HlhK1QKKlKCN0rYue_OkN5NmrpWohLaoWlB6oLMbsVn3M2fl_eAHygVbpQYQpbNMgg99jSa7LkOOh3Cggx49_6Rewzn02hrsC59Qo4O_WHIlgvwPnKlMCCOBIdEsELAbLV8hN_fd8nOC1RW9L57l90s5i_Z08BYvq6NrDz6-miPu-z2r_m6zov4vxtfsGSNFw</recordid><startdate>20170831</startdate><enddate>20170831</enddate><creator>Koldemir, Unsal</creator><creator>Tinkham, Jonathan S</creator><creator>Johnson, Robert</creator><creator>Lim, Bogyu</creator><creator>Yemam, Henok A</creator><creator>Gagnon, Kevin J</creator><creator>Parkin, Sean</creator><creator>Sellinger, Alan</creator><scope/></search><sort><creationdate>20170831</creationdate><title>Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a</title><author>Koldemir, Unsal ; Tinkham, Jonathan S ; Johnson, Robert ; Lim, Bogyu ; Yemam, Henok A ; Gagnon, Kevin J ; Parkin, Sean ; Sellinger, Alan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c7tc02528a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koldemir, Unsal</creatorcontrib><creatorcontrib>Tinkham, Jonathan S</creatorcontrib><creatorcontrib>Johnson, Robert</creatorcontrib><creatorcontrib>Lim, Bogyu</creatorcontrib><creatorcontrib>Yemam, Henok A</creatorcontrib><creatorcontrib>Gagnon, Kevin J</creatorcontrib><creatorcontrib>Parkin, Sean</creatorcontrib><creatorcontrib>Sellinger, Alan</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koldemir, Unsal</au><au>Tinkham, Jonathan S</au><au>Johnson, Robert</au><au>Lim, Bogyu</au><au>Yemam, Henok A</au><au>Gagnon, Kevin J</au><au>Parkin, Sean</au><au>Sellinger, Alan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a</atitle><date>2017-08-31</date><risdate>2017</risdate><volume>5</volume><issue>34</issue><spage>8723</spage><epage>8733</epage><pages>8723-8733</pages><issn>2050-7526</issn><eissn>2050-7534</eissn><abstract>A series of new polycyclic aromatic hydrocarbon compounds based on (4,10-disubstituted-dibenzo[def,mno]chrysene-6,12-dione) and 4,10 di-substituted 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture. Starting with an inexpensive commercially available textile dye known as Vat Orange #3, (4,10-dibromo-dibenzo[def,mno] chrysene-6,12-dione) we extended the conjugation at the 4- and 10-positions by the attachment of both electron rich and deficient hexylvinylphthalimide, thiophene, hexylthiophene, triphenylamine, and hexylbithiophene aromatic groups, and studied the resultant optoelectronic properties. By applying various synthetic metal-catalyzed reactions, soluble dibenzo[def,mno]chrysene and dibenzo[def,mno]chrysene-6,12-dione derivatives were achieved with optical edge band gaps between 2.30 eV and 1.65 eV.
Polycyclic aromatic hydrocarbon compounds based on 4,10 and 6,12-functionalized dibenzo[def,mno]chrysene are reported with tunable electronic properties through varied molecular architecture.</abstract><doi>10.1039/c7tc02528a</doi><tpages>11</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2050-7526 |
ispartof | |
issn | 2050-7526 2050-7534 |
language | eng |
recordid | cdi_rsc_primary_c7tc02528a |
source | Royal Society Of Chemistry Journals |
title | Orthogonal 4,10 and 6,12 substitution of dibenzo[def,mno]chrysene polycyclic aromatic small moleculesElectronic supplementary information (ESI) available. CCDC 1526927 and 1526928. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc02528a |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T04%3A07%3A16IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-rsc&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Orthogonal%204,10%20and%206,12%20substitution%20of%20dibenzo%5Bdef,mno%5Dchrysene%20polycyclic%20aromatic%20small%20moleculesElectronic%20supplementary%20information%20(ESI)%20available.%20CCDC%201526927%20and%201526928.%20For%20ESI%20and%20crystallographic%20data%20in%20CIF%20or%20other%20electronic%20format%20see%20DOI:%2010.1039/c7tc02528a&rft.au=Koldemir,%20Unsal&rft.date=2017-08-31&rft.volume=5&rft.issue=34&rft.spage=8723&rft.epage=8733&rft.pages=8723-8733&rft.issn=2050-7526&rft.eissn=2050-7534&rft_id=info:doi/10.1039/c7tc02528a&rft_dat=%3Crsc%3Ec7tc02528a%3C/rsc%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |