Photophysical Behavior of Self‐Organizing Derivatives of 10‐ and 12‐Vertex p‐Carboranes, and their Bicyclooctane and Benzene Analogues
Four series of isostructural derivatives of 3‐ring liquid crystalline derivatives containing p‐carboranes (12‐vertex A, and 10‐vertex B), bicyclo[2.2.2]octane (C), or benzene (D) as the variable structural element were investigated for their mesogenic behavior and electronic interactions. Comparativ...
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| Veröffentlicht in: | Chemistry : a European journal 2023-05, Vol.29 (30) |
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| creator | Jakubowski, Rafał Januszko, Adam Tilford, R William Radziszewski, George J Pietrzak, Anna Young, Victor G Kaszyński, Piotr |
| description | Four series of isostructural derivatives of 3‐ring liquid crystalline derivatives containing p‐carboranes (12‐vertex A, and 10‐vertex B), bicyclo[2.2.2]octane (C), or benzene (D) as the variable structural element were investigated for their mesogenic behavior and electronic interactions. Comparative studies demonstrated that the effectiveness of elements A–D in stabilization of the mesophase typically increases in the order: B |
| doi_str_mv | 10.1002/chem.202203948 |
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Comparative studies demonstrated that the effectiveness of elements A–D in stabilization of the mesophase typically increases in the order: B<A<C<D. Absorption and emission spectroscopy for the four series and reference compounds augmented with DFT computational results revealed that the degree of electronic interactions with the connected benzene π system increases in the order C<A<B<D. Emission spectra exhibit large Stokes’ shifts for 10‐vertex derivatives (B) in solutions and in the solid state. Spectroscopic characterization was supplemented with polarization electronic spectroscopy and solvatochromic studies of selected series. Overall, 12‐vertex p‐carborane A acts as an electron withdrawing auxochromic substituent with interactions similar to those of bicyclo[2.2.2]octane, although capable of accepting some electron density in the excited state. In contrast, 10‐vertex p‐carborane B is much more interactive with the π‐aromatic electron manifold and exhibits greater ability to participate in photo‐induced CT processes. Absorption and emission energies and quantum yields (1‐51 %) for carborane derivatives, representing the D−A−D system, were compared to those of their isoelectronic zwitterionic analogues (the A−D−A system). The analysis is supplemented with four single‐crystal XRD structures.]]></description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202203948</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Absorption ; Benzene ; Carborane ; Chemistry ; Comparative studies ; Electron density ; Electronic spectroscopy ; Emission spectra ; Emission spectroscopy ; Hydrocarbons ; Liquid crystals ; Spectrum analysis ; Structural members</subject><ispartof>Chemistry : a European journal, 2023-05, Vol.29 (30)</ispartof><rights>2023 Wiley‐VCH GmbH</rights><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>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Jakubowski, Rafał</creatorcontrib><creatorcontrib>Januszko, Adam</creatorcontrib><creatorcontrib>Tilford, R William</creatorcontrib><creatorcontrib>Radziszewski, George J</creatorcontrib><creatorcontrib>Pietrzak, Anna</creatorcontrib><creatorcontrib>Young, Victor G</creatorcontrib><creatorcontrib>Kaszyński, Piotr</creatorcontrib><title>Photophysical Behavior of Self‐Organizing Derivatives of 10‐ and 12‐Vertex p‐Carboranes, and their Bicyclooctane and Benzene Analogues</title><title>Chemistry : a European journal</title><description><![CDATA[Four series of isostructural derivatives of 3‐ring liquid crystalline derivatives containing p‐carboranes (12‐vertex A, and 10‐vertex B), bicyclo[2.2.2]octane (C), or benzene (D) as the variable structural element were investigated for their mesogenic behavior and electronic interactions. Comparative studies demonstrated that the effectiveness of elements A–D in stabilization of the mesophase typically increases in the order: B<A<C<D. Absorption and emission spectroscopy for the four series and reference compounds augmented with DFT computational results revealed that the degree of electronic interactions with the connected benzene π system increases in the order C<A<B<D. Emission spectra exhibit large Stokes’ shifts for 10‐vertex derivatives (B) in solutions and in the solid state. Spectroscopic characterization was supplemented with polarization electronic spectroscopy and solvatochromic studies of selected series. Overall, 12‐vertex p‐carborane A acts as an electron withdrawing auxochromic substituent with interactions similar to those of bicyclo[2.2.2]octane, although capable of accepting some electron density in the excited state. In contrast, 10‐vertex p‐carborane B is much more interactive with the π‐aromatic electron manifold and exhibits greater ability to participate in photo‐induced CT processes. Absorption and emission energies and quantum yields (1‐51 %) for carborane derivatives, representing the D−A−D system, were compared to those of their isoelectronic zwitterionic analogues (the A−D−A system). The analysis is supplemented with four single‐crystal XRD structures.]]></description><subject>Absorption</subject><subject>Benzene</subject><subject>Carborane</subject><subject>Chemistry</subject><subject>Comparative studies</subject><subject>Electron density</subject><subject>Electronic spectroscopy</subject><subject>Emission spectra</subject><subject>Emission spectroscopy</subject><subject>Hydrocarbons</subject><subject>Liquid crystals</subject><subject>Spectrum analysis</subject><subject>Structural members</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqNirtOwzAYRi0EEuGyMltiJcWXOK1HUorYQAKxVsb8iV0FO9huRDvxBIhn5EkwFQ_A9B195yB0RsmEEsIutYHXCSOMES6r2R4qqGC05NNa7KOCyGpa1oLLQ3QU44oQImvOC_R5b3zyg9lEq1WPGzBqtD5g3-IH6Nvvj6-70Clnt9Z1-BqCHVWyI8TfgJKssXIvmLJMTxASvOMh41yFZx-Ug3ix88mADbixeqN773XKZvc34LaQ-cqp3ndriCfooFV9hNO_PUbnN4vH-W05BP-WfVqu_DrkOi7ZjErGhKg4_1_1Ay9GXyw</recordid><startdate>20230501</startdate><enddate>20230501</enddate><creator>Jakubowski, Rafał</creator><creator>Januszko, Adam</creator><creator>Tilford, R William</creator><creator>Radziszewski, George J</creator><creator>Pietrzak, Anna</creator><creator>Young, Victor G</creator><creator>Kaszyński, Piotr</creator><general>Wiley Subscription Services, Inc</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope></search><sort><creationdate>20230501</creationdate><title>Photophysical Behavior of Self‐Organizing Derivatives of 10‐ and 12‐Vertex p‐Carboranes, and their Bicyclooctane and Benzene Analogues</title><author>Jakubowski, Rafał ; Januszko, Adam ; Tilford, R William ; Radziszewski, George J ; Pietrzak, Anna ; Young, Victor G ; Kaszyński, Piotr</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_journals_28192255433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Absorption</topic><topic>Benzene</topic><topic>Carborane</topic><topic>Chemistry</topic><topic>Comparative studies</topic><topic>Electron density</topic><topic>Electronic spectroscopy</topic><topic>Emission spectra</topic><topic>Emission spectroscopy</topic><topic>Hydrocarbons</topic><topic>Liquid crystals</topic><topic>Spectrum analysis</topic><topic>Structural members</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jakubowski, Rafał</creatorcontrib><creatorcontrib>Januszko, Adam</creatorcontrib><creatorcontrib>Tilford, R William</creatorcontrib><creatorcontrib>Radziszewski, George J</creatorcontrib><creatorcontrib>Pietrzak, Anna</creatorcontrib><creatorcontrib>Young, Victor G</creatorcontrib><creatorcontrib>Kaszyński, Piotr</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jakubowski, Rafał</au><au>Januszko, Adam</au><au>Tilford, R William</au><au>Radziszewski, George J</au><au>Pietrzak, Anna</au><au>Young, Victor G</au><au>Kaszyński, Piotr</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photophysical Behavior of Self‐Organizing Derivatives of 10‐ and 12‐Vertex p‐Carboranes, and their Bicyclooctane and Benzene Analogues</atitle><jtitle>Chemistry : a European journal</jtitle><date>2023-05-01</date><risdate>2023</risdate><volume>29</volume><issue>30</issue><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract><![CDATA[Four series of isostructural derivatives of 3‐ring liquid crystalline derivatives containing p‐carboranes (12‐vertex A, and 10‐vertex B), bicyclo[2.2.2]octane (C), or benzene (D) as the variable structural element were investigated for their mesogenic behavior and electronic interactions. Comparative studies demonstrated that the effectiveness of elements A–D in stabilization of the mesophase typically increases in the order: B<A<C<D. Absorption and emission spectroscopy for the four series and reference compounds augmented with DFT computational results revealed that the degree of electronic interactions with the connected benzene π system increases in the order C<A<B<D. Emission spectra exhibit large Stokes’ shifts for 10‐vertex derivatives (B) in solutions and in the solid state. Spectroscopic characterization was supplemented with polarization electronic spectroscopy and solvatochromic studies of selected series. Overall, 12‐vertex p‐carborane A acts as an electron withdrawing auxochromic substituent with interactions similar to those of bicyclo[2.2.2]octane, although capable of accepting some electron density in the excited state. In contrast, 10‐vertex p‐carborane B is much more interactive with the π‐aromatic electron manifold and exhibits greater ability to participate in photo‐induced CT processes. Absorption and emission energies and quantum yields (1‐51 %) for carborane derivatives, representing the D−A−D system, were compared to those of their isoelectronic zwitterionic analogues (the A−D−A system). The analysis is supplemented with four single‐crystal XRD structures.]]></abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.202203948</doi></addata></record> |
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| subjects | Absorption Benzene Carborane Chemistry Comparative studies Electron density Electronic spectroscopy Emission spectra Emission spectroscopy Hydrocarbons Liquid crystals Spectrum analysis Structural members |
| title | Photophysical Behavior of Self‐Organizing Derivatives of 10‐ and 12‐Vertex p‐Carboranes, and their Bicyclooctane and Benzene Analogues |
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