Effect of the phenoxy groups on PDIB and its derivatives
The anisotropic hole and electron mobilities in N , N ′-3,4,9,10-perylenediimide-1,7-phenoxy (PDIB-2OPh) and N , N ʹ-3,4,9,10-perylenediimide (PDIB) were theoretically predicted using the Marcus–Hush theory. The substituent effect of phenoxy on their mobility rates, absorption spectra, electron affi...
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| creator | Song, Peng Guan, Baijie Zhou, Qiao Zhao, Meiyu Huang, Jindou Ma, Fengcai |
| description | The anisotropic hole and electron mobilities in
N
,
N
′-3,4,9,10-perylenediimide-1,7-phenoxy (PDIB-2OPh) and
N
,
N
ʹ-3,4,9,10-perylenediimide (PDIB) were theoretically predicted using the Marcus–Hush theory. The substituent effect of phenoxy on their mobility rates, absorption spectra, electron affinities, and ionization potentials was explored. By comparing the simulated hole mobility in PDIB and PDIB-2OPh, it is found that the phenoxy rings act as spacers between adjacent stacking columns in the phenoxy-substituted derivatives. The increasement of the number of benzene oxygen groups leads to the absorption spectra red-shift of these molecular systems. This coincides with their change tendency of the adiabatic ionization potentials, vertical ionization potentials. However, the calculated adiabatic electron affinities and vertical electron affinities of
N
,
N
′-butyl-3,4,9,10-perylenediimide-1,6,7,12-phenoxy (PDIB-4OPh) are larger than those of PDIB;OPh. The steric effect in PDIB-4OPh is expected to cause space reversal and thus to changes in the properties of the molecule. |
| doi_str_mv | 10.1038/srep35555 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5069556</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1835488574</sourcerecordid><originalsourceid>FETCH-LOGICAL-c438t-f0917a37f51f6e2bfe471505192db56f8a52c1dfe73f650b15ffa444a771e7223</originalsourceid><addsrcrecordid>eNplkU1LAzEQhoMoKurBPyABLypU8zWb3Yug9RMEPeg5pLuTdqXdrMlu0X9vpFqqzmUG5uGdj5eQfc5OOZP5WQzYSkixRrYFUzAQUoj1lXqL7MX4ylKAKBQvNsmW0BoKBmyb5NfOYdlR72g3QdpOsPHvH3QcfN9G6hv6dHV_SW1T0bqLtMJQz21XzzHukg1npxH3vvMOebm5fh7eDR4eb--HFw-DUsm8GzhWcG2ldsBdhmLkUGkODHghqhFkLrcgSl451NJlwEYcnLNKKas1Ry2E3CHnC922H82wKrHpgp2aNtQzGz6Mt7X53WnqiRn7uQGWFQBZEjj6Fgj-rcfYmVkdS5xObYO-j4bnElSeg1YJPfyDvvo-NOm8RBUF50zlMlHHC6oMPqbvu-UynJkvS8zSksQerG6_JH8MSMDJAoip1YwxrIz8p_YJPgWT3A</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1899110483</pqid></control><display><type>article</type><title>Effect of the phenoxy groups on PDIB and its derivatives</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Springer Nature OA Free Journals</source><source>Nature Free</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><creator>Song, Peng ; Guan, Baijie ; Zhou, Qiao ; Zhao, Meiyu ; Huang, Jindou ; Ma, Fengcai</creator><creatorcontrib>Song, Peng ; Guan, Baijie ; Zhou, Qiao ; Zhao, Meiyu ; Huang, Jindou ; Ma, Fengcai</creatorcontrib><description>The anisotropic hole and electron mobilities in
N
,
N
′-3,4,9,10-perylenediimide-1,7-phenoxy (PDIB-2OPh) and
N
,
N
ʹ-3,4,9,10-perylenediimide (PDIB) were theoretically predicted using the Marcus–Hush theory. The substituent effect of phenoxy on their mobility rates, absorption spectra, electron affinities, and ionization potentials was explored. By comparing the simulated hole mobility in PDIB and PDIB-2OPh, it is found that the phenoxy rings act as spacers between adjacent stacking columns in the phenoxy-substituted derivatives. The increasement of the number of benzene oxygen groups leads to the absorption spectra red-shift of these molecular systems. This coincides with their change tendency of the adiabatic ionization potentials, vertical ionization potentials. However, the calculated adiabatic electron affinities and vertical electron affinities of
N
,
N
′-butyl-3,4,9,10-perylenediimide-1,6,7,12-phenoxy (PDIB-4OPh) are larger than those of PDIB;OPh. The steric effect in PDIB-4OPh is expected to cause space reversal and thus to changes in the properties of the molecule.</description><identifier>ISSN: 2045-2322</identifier><identifier>EISSN: 2045-2322</identifier><identifier>DOI: 10.1038/srep35555</identifier><identifier>PMID: 27759050</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>639/301 ; 639/766 ; Absorption ; Adiabatic ; Benzene ; Crystals ; Humanities and Social Sciences ; Ionization ; Mobility ; multidisciplinary ; Science ; Transistors</subject><ispartof>Scientific reports, 2016-10, Vol.6 (1), p.35555-35555, Article 35555</ispartof><rights>The Author(s) 2016</rights><rights>Copyright Nature Publishing Group Oct 2016</rights><rights>Copyright © 2016, The Author(s) 2016 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-f0917a37f51f6e2bfe471505192db56f8a52c1dfe73f650b15ffa444a771e7223</citedby><cites>FETCH-LOGICAL-c438t-f0917a37f51f6e2bfe471505192db56f8a52c1dfe73f650b15ffa444a771e7223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5069556/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5069556/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,41120,42189,51576,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27759050$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Song, Peng</creatorcontrib><creatorcontrib>Guan, Baijie</creatorcontrib><creatorcontrib>Zhou, Qiao</creatorcontrib><creatorcontrib>Zhao, Meiyu</creatorcontrib><creatorcontrib>Huang, Jindou</creatorcontrib><creatorcontrib>Ma, Fengcai</creatorcontrib><title>Effect of the phenoxy groups on PDIB and its derivatives</title><title>Scientific reports</title><addtitle>Sci Rep</addtitle><addtitle>Sci Rep</addtitle><description>The anisotropic hole and electron mobilities in
N
,
N
′-3,4,9,10-perylenediimide-1,7-phenoxy (PDIB-2OPh) and
N
,
N
ʹ-3,4,9,10-perylenediimide (PDIB) were theoretically predicted using the Marcus–Hush theory. The substituent effect of phenoxy on their mobility rates, absorption spectra, electron affinities, and ionization potentials was explored. By comparing the simulated hole mobility in PDIB and PDIB-2OPh, it is found that the phenoxy rings act as spacers between adjacent stacking columns in the phenoxy-substituted derivatives. The increasement of the number of benzene oxygen groups leads to the absorption spectra red-shift of these molecular systems. This coincides with their change tendency of the adiabatic ionization potentials, vertical ionization potentials. However, the calculated adiabatic electron affinities and vertical electron affinities of
N
,
N
′-butyl-3,4,9,10-perylenediimide-1,6,7,12-phenoxy (PDIB-4OPh) are larger than those of PDIB;OPh. The steric effect in PDIB-4OPh is expected to cause space reversal and thus to changes in the properties of the molecule.</description><subject>639/301</subject><subject>639/766</subject><subject>Absorption</subject><subject>Adiabatic</subject><subject>Benzene</subject><subject>Crystals</subject><subject>Humanities and Social Sciences</subject><subject>Ionization</subject><subject>Mobility</subject><subject>multidisciplinary</subject><subject>Science</subject><subject>Transistors</subject><issn>2045-2322</issn><issn>2045-2322</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNplkU1LAzEQhoMoKurBPyABLypU8zWb3Yug9RMEPeg5pLuTdqXdrMlu0X9vpFqqzmUG5uGdj5eQfc5OOZP5WQzYSkixRrYFUzAQUoj1lXqL7MX4ylKAKBQvNsmW0BoKBmyb5NfOYdlR72g3QdpOsPHvH3QcfN9G6hv6dHV_SW1T0bqLtMJQz21XzzHukg1npxH3vvMOebm5fh7eDR4eb--HFw-DUsm8GzhWcG2ldsBdhmLkUGkODHghqhFkLrcgSl451NJlwEYcnLNKKas1Ry2E3CHnC922H82wKrHpgp2aNtQzGz6Mt7X53WnqiRn7uQGWFQBZEjj6Fgj-rcfYmVkdS5xObYO-j4bnElSeg1YJPfyDvvo-NOm8RBUF50zlMlHHC6oMPqbvu-UynJkvS8zSksQerG6_JH8MSMDJAoip1YwxrIz8p_YJPgWT3A</recordid><startdate>20161019</startdate><enddate>20161019</enddate><creator>Song, Peng</creator><creator>Guan, Baijie</creator><creator>Zhou, Qiao</creator><creator>Zhao, Meiyu</creator><creator>Huang, Jindou</creator><creator>Ma, Fengcai</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20161019</creationdate><title>Effect of the phenoxy groups on PDIB and its derivatives</title><author>Song, Peng ; Guan, Baijie ; Zhou, Qiao ; Zhao, Meiyu ; Huang, Jindou ; Ma, Fengcai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-f0917a37f51f6e2bfe471505192db56f8a52c1dfe73f650b15ffa444a771e7223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>639/301</topic><topic>639/766</topic><topic>Absorption</topic><topic>Adiabatic</topic><topic>Benzene</topic><topic>Crystals</topic><topic>Humanities and Social Sciences</topic><topic>Ionization</topic><topic>Mobility</topic><topic>multidisciplinary</topic><topic>Science</topic><topic>Transistors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Peng</creatorcontrib><creatorcontrib>Guan, Baijie</creatorcontrib><creatorcontrib>Zhou, Qiao</creatorcontrib><creatorcontrib>Zhao, Meiyu</creatorcontrib><creatorcontrib>Huang, Jindou</creatorcontrib><creatorcontrib>Ma, Fengcai</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Scientific reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Song, Peng</au><au>Guan, Baijie</au><au>Zhou, Qiao</au><au>Zhao, Meiyu</au><au>Huang, Jindou</au><au>Ma, Fengcai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of the phenoxy groups on PDIB and its derivatives</atitle><jtitle>Scientific reports</jtitle><stitle>Sci Rep</stitle><addtitle>Sci Rep</addtitle><date>2016-10-19</date><risdate>2016</risdate><volume>6</volume><issue>1</issue><spage>35555</spage><epage>35555</epage><pages>35555-35555</pages><artnum>35555</artnum><issn>2045-2322</issn><eissn>2045-2322</eissn><abstract>The anisotropic hole and electron mobilities in
N
,
N
′-3,4,9,10-perylenediimide-1,7-phenoxy (PDIB-2OPh) and
N
,
N
ʹ-3,4,9,10-perylenediimide (PDIB) were theoretically predicted using the Marcus–Hush theory. The substituent effect of phenoxy on their mobility rates, absorption spectra, electron affinities, and ionization potentials was explored. By comparing the simulated hole mobility in PDIB and PDIB-2OPh, it is found that the phenoxy rings act as spacers between adjacent stacking columns in the phenoxy-substituted derivatives. The increasement of the number of benzene oxygen groups leads to the absorption spectra red-shift of these molecular systems. This coincides with their change tendency of the adiabatic ionization potentials, vertical ionization potentials. However, the calculated adiabatic electron affinities and vertical electron affinities of
N
,
N
′-butyl-3,4,9,10-perylenediimide-1,6,7,12-phenoxy (PDIB-4OPh) are larger than those of PDIB;OPh. The steric effect in PDIB-4OPh is expected to cause space reversal and thus to changes in the properties of the molecule.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>27759050</pmid><doi>10.1038/srep35555</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Springer Nature OA Free Journals; Nature Free; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | 639/301 639/766 Absorption Adiabatic Benzene Crystals Humanities and Social Sciences Ionization Mobility multidisciplinary Science Transistors |
| title | Effect of the phenoxy groups on PDIB and its derivatives |
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