Saddle-Shaped Cyclic Indole Tetramers: 3D Electroactive Molecules
We present a joint theoretical and experimental study of a series of cyclic indole tetramers aimed at understanding the fundamental electronic properties of this 3D platform and evaluating its potential in the construction of new semiconductors. To this end, we combined absorption and Raman spectros...
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| Veröffentlicht in: | Chemistry : a European journal 2016-07, Vol.22 (30), p.10651-10660 |
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| creator | Ruiz, Constanza Monge, Ángeles Gutiérrez-Puebla, Enrique Alkorta, Ibon Elguero, José Navarrete, Juan T. López Ruiz Delgado, M. Carmen Gómez-Lor, Berta |
| description | We present a joint theoretical and experimental study of a series of cyclic indole tetramers aimed at understanding the fundamental electronic properties of this 3D platform and evaluating its potential in the construction of new semiconductors. To this end, we combined absorption and Raman spectroscopy, cyclic voltammetry, and spectroelectrochemistry with DFT calculations. Our results suggest that this platform can be easily and reversibly oxidized. Additionally, it has a HOMO that matches very well with the workfunction of gold, therefore charge injection from a gold electrode is expected to occur without significant barriers. Interestingly, the cyclic tetraindoles allow for good electron delocalization in spite of their saddle‐shaped structures. The steric constraints introduced by N‐substitution significantly inhibits ring inversion of the central cyclooctatetraene unit, whereas it only barely affects the optical and electrochemical properties (a slightly higher oxidation potential and a blueshifted absorption upon alkylation are observed).
Cyclic tetraindoles that allow for efficient electronic communication among their branches represent interesting 3D electroactive scaffolds with potential applications in organic electronics (see figure). |
| doi_str_mv | 10.1002/chem.201600932 |
| format | Article |
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Cyclic tetraindoles that allow for efficient electronic communication among their branches represent interesting 3D electroactive scaffolds with potential applications in organic electronics (see figure).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201600932</identifier><identifier>PMID: 27320301</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Absorption ; Alkylation ; Charge injection ; Chemistry ; Construction ; cyclooctatetraene ; Electrochemical analysis ; Electrochemistry ; Electrode potentials ; Electrodes ; Electronic properties ; Electronics ; Electronics industry ; Gold ; hyperconjugation ; Indoles ; Injection ; Inversion ; Inversions ; Mathematical analysis ; Optical properties ; organic semiconductors ; Oxidation ; Platforms ; Raman spectroscopy ; Semiconductors ; spectroelectrochemistry ; Spectroscopy ; tetraindoles ; Voltammetry</subject><ispartof>Chemistry : a European journal, 2016-07, Vol.22 (30), p.10651-10660</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5092-26ca2cb0991e42e309dc903b6b7800e0a27b833f1f4a962f30d83df1ca90b0063</citedby><cites>FETCH-LOGICAL-c5092-26ca2cb0991e42e309dc903b6b7800e0a27b833f1f4a962f30d83df1ca90b0063</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201600932$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201600932$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27320301$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ruiz, Constanza</creatorcontrib><creatorcontrib>Monge, Ángeles</creatorcontrib><creatorcontrib>Gutiérrez-Puebla, Enrique</creatorcontrib><creatorcontrib>Alkorta, Ibon</creatorcontrib><creatorcontrib>Elguero, José</creatorcontrib><creatorcontrib>Navarrete, Juan T. López</creatorcontrib><creatorcontrib>Ruiz Delgado, M. Carmen</creatorcontrib><creatorcontrib>Gómez-Lor, Berta</creatorcontrib><title>Saddle-Shaped Cyclic Indole Tetramers: 3D Electroactive Molecules</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>We present a joint theoretical and experimental study of a series of cyclic indole tetramers aimed at understanding the fundamental electronic properties of this 3D platform and evaluating its potential in the construction of new semiconductors. To this end, we combined absorption and Raman spectroscopy, cyclic voltammetry, and spectroelectrochemistry with DFT calculations. Our results suggest that this platform can be easily and reversibly oxidized. Additionally, it has a HOMO that matches very well with the workfunction of gold, therefore charge injection from a gold electrode is expected to occur without significant barriers. Interestingly, the cyclic tetraindoles allow for good electron delocalization in spite of their saddle‐shaped structures. The steric constraints introduced by N‐substitution significantly inhibits ring inversion of the central cyclooctatetraene unit, whereas it only barely affects the optical and electrochemical properties (a slightly higher oxidation potential and a blueshifted absorption upon alkylation are observed).
Cyclic tetraindoles that allow for efficient electronic communication among their branches represent interesting 3D electroactive scaffolds with potential applications in organic electronics (see figure).</description><subject>Absorption</subject><subject>Alkylation</subject><subject>Charge injection</subject><subject>Chemistry</subject><subject>Construction</subject><subject>cyclooctatetraene</subject><subject>Electrochemical analysis</subject><subject>Electrochemistry</subject><subject>Electrode potentials</subject><subject>Electrodes</subject><subject>Electronic properties</subject><subject>Electronics</subject><subject>Electronics industry</subject><subject>Gold</subject><subject>hyperconjugation</subject><subject>Indoles</subject><subject>Injection</subject><subject>Inversion</subject><subject>Inversions</subject><subject>Mathematical analysis</subject><subject>Optical properties</subject><subject>organic semiconductors</subject><subject>Oxidation</subject><subject>Platforms</subject><subject>Raman spectroscopy</subject><subject>Semiconductors</subject><subject>spectroelectrochemistry</subject><subject>Spectroscopy</subject><subject>tetraindoles</subject><subject>Voltammetry</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqN0c1v1DAQBXALgehSuHJEkbhwyTL2xHbMrdou20otXy1C4mI5zkRNcTaLnbTsf0-qLSvEATjN5feeNHqMPecw5wDitb-ibi6AKwCD4gGbcSl4jlrJh2wGptC5kmgO2JOUrmEyCvExOxAaBSDwGTu6cHUdKL-4chuqs8XWh9Znp-u6D5Rd0hBdRzG9yfA4WwbyQ-ydH9obys4n4MdA6Sl71LiQ6Nn9PWSf3y4vFyf52fvV6eLoLPcSjMiF8k74CozhVAhCMLU3gJWqdAlA4ISuSsSGN4UzSjQIdYl1w70zUAEoPGSvdr2b2H8fKQ22a5OnENya-jFZXqKUUnFh_oNCUUqjtZjoyz_odT_G9fSI5Qa0lFwJ-VdVAiptClFOar5TPvYpRWrsJradi1vLwd6tZe_Wsvu1psCL-9qx6qje81_zTMDswG0baPuPOrs4WZ7_Xp7vsm0a6Mc-6-I3qzRqab-8W9mvn_SHY_wIdoU_Af1Oq80</recordid><startdate>20160718</startdate><enddate>20160718</enddate><creator>Ruiz, Constanza</creator><creator>Monge, Ángeles</creator><creator>Gutiérrez-Puebla, Enrique</creator><creator>Alkorta, Ibon</creator><creator>Elguero, José</creator><creator>Navarrete, Juan T. López</creator><creator>Ruiz Delgado, M. Carmen</creator><creator>Gómez-Lor, Berta</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160718</creationdate><title>Saddle-Shaped Cyclic Indole Tetramers: 3D Electroactive Molecules</title><author>Ruiz, Constanza ; Monge, Ángeles ; Gutiérrez-Puebla, Enrique ; Alkorta, Ibon ; Elguero, José ; Navarrete, Juan T. López ; Ruiz Delgado, M. Carmen ; Gómez-Lor, Berta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5092-26ca2cb0991e42e309dc903b6b7800e0a27b833f1f4a962f30d83df1ca90b0063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Absorption</topic><topic>Alkylation</topic><topic>Charge injection</topic><topic>Chemistry</topic><topic>Construction</topic><topic>cyclooctatetraene</topic><topic>Electrochemical analysis</topic><topic>Electrochemistry</topic><topic>Electrode potentials</topic><topic>Electrodes</topic><topic>Electronic properties</topic><topic>Electronics</topic><topic>Electronics industry</topic><topic>Gold</topic><topic>hyperconjugation</topic><topic>Indoles</topic><topic>Injection</topic><topic>Inversion</topic><topic>Inversions</topic><topic>Mathematical analysis</topic><topic>Optical properties</topic><topic>organic semiconductors</topic><topic>Oxidation</topic><topic>Platforms</topic><topic>Raman spectroscopy</topic><topic>Semiconductors</topic><topic>spectroelectrochemistry</topic><topic>Spectroscopy</topic><topic>tetraindoles</topic><topic>Voltammetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ruiz, Constanza</creatorcontrib><creatorcontrib>Monge, Ángeles</creatorcontrib><creatorcontrib>Gutiérrez-Puebla, Enrique</creatorcontrib><creatorcontrib>Alkorta, Ibon</creatorcontrib><creatorcontrib>Elguero, José</creatorcontrib><creatorcontrib>Navarrete, Juan T. 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Additionally, it has a HOMO that matches very well with the workfunction of gold, therefore charge injection from a gold electrode is expected to occur without significant barriers. Interestingly, the cyclic tetraindoles allow for good electron delocalization in spite of their saddle‐shaped structures. The steric constraints introduced by N‐substitution significantly inhibits ring inversion of the central cyclooctatetraene unit, whereas it only barely affects the optical and electrochemical properties (a slightly higher oxidation potential and a blueshifted absorption upon alkylation are observed).
Cyclic tetraindoles that allow for efficient electronic communication among their branches represent interesting 3D electroactive scaffolds with potential applications in organic electronics (see figure).</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27320301</pmid><doi>10.1002/chem.201600932</doi><tpages>10</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Absorption Alkylation Charge injection Chemistry Construction cyclooctatetraene Electrochemical analysis Electrochemistry Electrode potentials Electrodes Electronic properties Electronics Electronics industry Gold hyperconjugation Indoles Injection Inversion Inversions Mathematical analysis Optical properties organic semiconductors Oxidation Platforms Raman spectroscopy Semiconductors spectroelectrochemistry Spectroscopy tetraindoles Voltammetry |
| title | Saddle-Shaped Cyclic Indole Tetramers: 3D Electroactive Molecules |
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