Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines

Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines

A synthetic route to fused bisphenazine compounds has been developed. Thus, 2,7-di-tert-butyl-quinoxalino[2‘,3‘,9,10]phenanthro[4,5-abc]phenazine-6,7,15,16-tetraalkoxy compounds have been synthesized in good yields. The structures of these new compounds were ascertained by nuclear magnetic resonance...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry of materials 2004-11, Vol.16 (24), p.4912-4915
Hauptverfasser: Hu, Jie, Zhang, Dong, Jin, Shi, Cheng, Stephen Z. D., Harris, Frank W.
Format: Artikel
Sprache:eng
Schlagworte:
Applied sciences
Chemistry
Condensed matter: electronic structure, electrical, magnetic, and optical properties
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
General and physical chemistry
Physicochemistry of polymers
Physics
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4915
container_issue 24
container_start_page 4912
container_title Chemistry of materials
container_volume 16
creator Hu, Jie
Zhang, Dong
Jin, Shi
Cheng, Stephen Z. D.
Harris, Frank W.
description A synthetic route to fused bisphenazine compounds has been developed. Thus, 2,7-di-tert-butyl-quinoxalino[2‘,3‘,9,10]phenanthro[4,5-abc]phenazine-6,7,15,16-tetraalkoxy compounds have been synthesized in good yields. The structures of these new compounds were ascertained by nuclear magnetic resonance (NMR) and mass spectroscopy. Differential scanning calorimetry (DSC), polarized light microscopy (PLM), and wide-angle X-ray diffraction (WAXD) studies showed that some of these planar molecules display liquid crystalline phases at elevated temperatures. WAXD analysis also indicated that the molecules undergo π−π stacking in the liquid crystalline phase. Differential pulse voltammetry (DPV) showed that the compounds undergo two reduction processes. Thus, it is speculated that the materials have potential as electron transporting materials in electronic devices such as organic photovoltaic or light-emitting diodes.
doi_str_mv 10.1021/cm0492179
format Article
fullrecord <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_cm0492179</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_TPS_GLHTGLKF_M</sourcerecordid><originalsourceid>FETCH-LOGICAL-a391t-2b55eac182424b69983df46f012d6db69715fb3a943113b251472279f57a382a3</originalsourceid><addsrcrecordid>eNptkD9PwzAQxS0EEqUw8A2yMDAY_CeO4xEi2iKCqNQyW5fEVl3SJNipRPn0pCqiC9Pp7n73nt4hdE3JHSWM3pcbEitGpTpBIyoYwYIQdopGJFUSx1Ik5-gihDUhdMDTEcoWu6ZfmeBCBE0VzX3bGd87E6LWRvMaGvBR7j63rsKZ34Ue6to1Jnp0oVuZBr6HJlyiMwt1MFe_dYzeJ0_LbIbzt-lz9pBj4Ir2mBVCGChpymIWF4lSKa9snFhCWZVUw0BSYQsOKuaU8oIJGkvGpLJCAk8Z8DG6PeiWvg3BG6s77zbgd5oSvU-v_9IP7M2B7SCUUFsPTenC8SDhw0fSPYcPnAu9-frbg__QieRS6OV8oaf5bDnNXyb69agLZdDrduubIfE__j-dkHOF</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines</title><source>American Chemical Society Journals</source><creator>Hu, Jie ; Zhang, Dong ; Jin, Shi ; Cheng, Stephen Z. D. ; Harris, Frank W.</creator><creatorcontrib>Hu, Jie ; Zhang, Dong ; Jin, Shi ; Cheng, Stephen Z. D. ; Harris, Frank W.</creatorcontrib><description>A synthetic route to fused bisphenazine compounds has been developed. Thus, 2,7-di-tert-butyl-quinoxalino[2‘,3‘,9,10]phenanthro[4,5-abc]phenazine-6,7,15,16-tetraalkoxy compounds have been synthesized in good yields. The structures of these new compounds were ascertained by nuclear magnetic resonance (NMR) and mass spectroscopy. Differential scanning calorimetry (DSC), polarized light microscopy (PLM), and wide-angle X-ray diffraction (WAXD) studies showed that some of these planar molecules display liquid crystalline phases at elevated temperatures. WAXD analysis also indicated that the molecules undergo π−π stacking in the liquid crystalline phase. Differential pulse voltammetry (DPV) showed that the compounds undergo two reduction processes. Thus, it is speculated that the materials have potential as electron transporting materials in electronic devices such as organic photovoltaic or light-emitting diodes.</description><identifier>ISSN: 0897-4756</identifier><identifier>EISSN: 1520-5002</identifier><identifier>DOI: 10.1021/cm0492179</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Chemistry ; Condensed matter: electronic structure, electrical, magnetic, and optical properties ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; General and physical chemistry ; Physicochemistry of polymers ; Physics</subject><ispartof>Chemistry of materials, 2004-11, Vol.16 (24), p.4912-4915</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a391t-2b55eac182424b69983df46f012d6db69715fb3a943113b251472279f57a382a3</citedby><cites>FETCH-LOGICAL-a391t-2b55eac182424b69983df46f012d6db69715fb3a943113b251472279f57a382a3</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/cm0492179$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/cm0492179$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=16308989$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Hu, Jie</creatorcontrib><creatorcontrib>Zhang, Dong</creatorcontrib><creatorcontrib>Jin, Shi</creatorcontrib><creatorcontrib>Cheng, Stephen Z. D.</creatorcontrib><creatorcontrib>Harris, Frank W.</creatorcontrib><title>Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines</title><title>Chemistry of materials</title><addtitle>Chem. Mater</addtitle><description>A synthetic route to fused bisphenazine compounds has been developed. Thus, 2,7-di-tert-butyl-quinoxalino[2‘,3‘,9,10]phenanthro[4,5-abc]phenazine-6,7,15,16-tetraalkoxy compounds have been synthesized in good yields. The structures of these new compounds were ascertained by nuclear magnetic resonance (NMR) and mass spectroscopy. Differential scanning calorimetry (DSC), polarized light microscopy (PLM), and wide-angle X-ray diffraction (WAXD) studies showed that some of these planar molecules display liquid crystalline phases at elevated temperatures. WAXD analysis also indicated that the molecules undergo π−π stacking in the liquid crystalline phase. Differential pulse voltammetry (DPV) showed that the compounds undergo two reduction processes. Thus, it is speculated that the materials have potential as electron transporting materials in electronic devices such as organic photovoltaic or light-emitting diodes.</description><subject>Applied sciences</subject><subject>Chemistry</subject><subject>Condensed matter: electronic structure, electrical, magnetic, and optical properties</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Physicochemistry of polymers</subject><subject>Physics</subject><issn>0897-4756</issn><issn>1520-5002</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkD9PwzAQxS0EEqUw8A2yMDAY_CeO4xEi2iKCqNQyW5fEVl3SJNipRPn0pCqiC9Pp7n73nt4hdE3JHSWM3pcbEitGpTpBIyoYwYIQdopGJFUSx1Ik5-gihDUhdMDTEcoWu6ZfmeBCBE0VzX3bGd87E6LWRvMaGvBR7j63rsKZ34Ue6to1Jnp0oVuZBr6HJlyiMwt1MFe_dYzeJ0_LbIbzt-lz9pBj4Ir2mBVCGChpymIWF4lSKa9snFhCWZVUw0BSYQsOKuaU8oIJGkvGpLJCAk8Z8DG6PeiWvg3BG6s77zbgd5oSvU-v_9IP7M2B7SCUUFsPTenC8SDhw0fSPYcPnAu9-frbg__QieRS6OV8oaf5bDnNXyb69agLZdDrduubIfE__j-dkHOF</recordid><startdate>20041130</startdate><enddate>20041130</enddate><creator>Hu, Jie</creator><creator>Zhang, Dong</creator><creator>Jin, Shi</creator><creator>Cheng, Stephen Z. D.</creator><creator>Harris, Frank W.</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20041130</creationdate><title>Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines</title><author>Hu, Jie ; Zhang, Dong ; Jin, Shi ; Cheng, Stephen Z. D. ; Harris, Frank W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a391t-2b55eac182424b69983df46f012d6db69715fb3a943113b251472279f57a382a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Applied sciences</topic><topic>Chemistry</topic><topic>Condensed matter: electronic structure, electrical, magnetic, and optical properties</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Physicochemistry of polymers</topic><topic>Physics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Jie</creatorcontrib><creatorcontrib>Zhang, Dong</creatorcontrib><creatorcontrib>Jin, Shi</creatorcontrib><creatorcontrib>Cheng, Stephen Z. D.</creatorcontrib><creatorcontrib>Harris, Frank W.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemistry of materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Jie</au><au>Zhang, Dong</au><au>Jin, Shi</au><au>Cheng, Stephen Z. D.</au><au>Harris, Frank W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines</atitle><jtitle>Chemistry of materials</jtitle><addtitle>Chem. Mater</addtitle><date>2004-11-30</date><risdate>2004</risdate><volume>16</volume><issue>24</issue><spage>4912</spage><epage>4915</epage><pages>4912-4915</pages><issn>0897-4756</issn><eissn>1520-5002</eissn><abstract>A synthetic route to fused bisphenazine compounds has been developed. Thus, 2,7-di-tert-butyl-quinoxalino[2‘,3‘,9,10]phenanthro[4,5-abc]phenazine-6,7,15,16-tetraalkoxy compounds have been synthesized in good yields. The structures of these new compounds were ascertained by nuclear magnetic resonance (NMR) and mass spectroscopy. Differential scanning calorimetry (DSC), polarized light microscopy (PLM), and wide-angle X-ray diffraction (WAXD) studies showed that some of these planar molecules display liquid crystalline phases at elevated temperatures. WAXD analysis also indicated that the molecules undergo π−π stacking in the liquid crystalline phase. Differential pulse voltammetry (DPV) showed that the compounds undergo two reduction processes. Thus, it is speculated that the materials have potential as electron transporting materials in electronic devices such as organic photovoltaic or light-emitting diodes.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/cm0492179</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0897-4756
ispartof Chemistry of materials, 2004-11, Vol.16 (24), p.4912-4915
issn 0897-4756
1520-5002
language eng
recordid cdi_crossref_primary_10_1021_cm0492179
source American Chemical Society Journals
subjects Applied sciences
Chemistry
Condensed matter: electronic structure, electrical, magnetic, and optical properties
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
General and physical chemistry
Physicochemistry of polymers
Physics
title Synthesis and Properties of Planar Liquid-Crystalline Bisphenazines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T20%3A13%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20Properties%20of%20Planar%20Liquid-Crystalline%20Bisphenazines&rft.jtitle=Chemistry%20of%20materials&rft.au=Hu,%20Jie&rft.date=2004-11-30&rft.volume=16&rft.issue=24&rft.spage=4912&rft.epage=4915&rft.pages=4912-4915&rft.issn=0897-4756&rft.eissn=1520-5002&rft_id=info:doi/10.1021/cm0492179&rft_dat=%3Cistex_cross%3Eark_67375_TPS_GLHTGLKF_M%3C/istex_cross%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