Synthesis of Shape-Persistent Macrocycles with Three 1,8-Diazaanthracene Units and Their Packing in the Single Crystal
The synthesis of four shape‐persistent macrocycles with three 1,8‐diazaanthracene units each is reported (2,3 a–3 c). For two of them single crystals could be obtained and the structures in the crystal be solved. The structures reveal that macrocycle 2 self‐dimerizes in the solid state; surprisingly...
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| Veröffentlicht in: | Chemistry : a European journal 2013-09, Vol.19 (40), p.13348-13354 |
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| container_title | Chemistry : a European journal |
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| creator | Li, Ming Klärner, Frank-Gerrit Sakamoto, Junji Schlüter, A. Dieter |
| description | The synthesis of four shape‐persistent macrocycles with three 1,8‐diazaanthracene units each is reported (2,3 a–3 c). For two of them single crystals could be obtained and the structures in the crystal be solved. The structures reveal that macrocycle 2 self‐dimerizes in the solid state; surprisingly it also forms a stable dimer in solution. The reason for this is seen in unusually efficient dispersion interactions as a consequence of the large contact areas in the dimer. All macrocycles are assessed as to their applicability in lateral polymerizations in the single crystal as well as in solution.
The perfect fit: Two shape‐persistent macrocycles such as A form a self‐assembled dimer in the single crystal which even under forcing conditions in solution cannot be made to dissociate into the single components. |
| doi_str_mv | 10.1002/chem.201301798 |
| format | Article |
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The perfect fit: Two shape‐persistent macrocycles such as A form a self‐assembled dimer in the single crystal which even under forcing conditions in solution cannot be made to dissociate into the single components.</description><subject>Chemistry</subject><subject>Contact</subject><subject>crystal packing</subject><subject>Crystal structure</subject><subject>Dimers</subject><subject>Dispersions</subject><subject>macrocycles</subject><subject>Macrocyclic compounds</subject><subject>Molecular structure</subject><subject>Polymerization</subject><subject>shape-persistence</subject><subject>Single crystals</subject><subject>supramolecular self-dimerization</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqNkUtvEzEURi0EoqGwZYkssWHBBL9mbC9R6AOpKUVpVXaWx7nDuJ14gj2hnf56HKVEiA2sfC2d77uyD0KvKZlSQtgH18JqygjlhEqtnqAJLRktuKzKp2hCtJBFVXJ9gF6kdEMI0RXnz9EBE4QrQfUE_VyMYWgh-YT7Bi9au4biAmK-DxAGPLcu9m50HSR854cWX7YRANP3qvjk7YO1ORytgwD4KvghYRuWmQEf8YV1tz58xz7gvAAv8twBnsUxDbZ7iZ41tkvw6vE8RFfHR5ez0-Lsy8nn2cezwglFVVELSgWrFUDDnQPlam4b7RqrNUDdgCK2roSjIBirXAlLXXJnhajBMSlB8UP0bte7jv2PDaTBrHxy0HU2QL9JhkqpCM_sf6CCq7JShJKMvv0Lvek3MeSHbClJtWSSZmq6o_IXphShMevoVzaOhhKzlWe28sxeXg68eazd1CtY7vHftjKgd8Cd72D8R52ZnR7N_ywvdtmt2ft91sZbU0kuS3N9fmKOhfgm5-fX5iv_BfK9tes</recordid><startdate>20130927</startdate><enddate>20130927</enddate><creator>Li, Ming</creator><creator>Klärner, Frank-Gerrit</creator><creator>Sakamoto, Junji</creator><creator>Schlüter, A. Dieter</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</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>20130927</creationdate><title>Synthesis of Shape-Persistent Macrocycles with Three 1,8-Diazaanthracene Units and Their Packing in the Single Crystal</title><author>Li, Ming ; Klärner, Frank-Gerrit ; Sakamoto, Junji ; Schlüter, A. Dieter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4818-b41142b8eef3cce8cb3af9cfa99eebfe80ab64c1e4226c5ed953ca44bec277e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Chemistry</topic><topic>Contact</topic><topic>crystal packing</topic><topic>Crystal structure</topic><topic>Dimers</topic><topic>Dispersions</topic><topic>macrocycles</topic><topic>Macrocyclic compounds</topic><topic>Molecular structure</topic><topic>Polymerization</topic><topic>shape-persistence</topic><topic>Single crystals</topic><topic>supramolecular self-dimerization</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Ming</creatorcontrib><creatorcontrib>Klärner, Frank-Gerrit</creatorcontrib><creatorcontrib>Sakamoto, Junji</creatorcontrib><creatorcontrib>Schlüter, A. Dieter</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><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><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Ming</au><au>Klärner, Frank-Gerrit</au><au>Sakamoto, Junji</au><au>Schlüter, A. Dieter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Shape-Persistent Macrocycles with Three 1,8-Diazaanthracene Units and Their Packing in the Single Crystal</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2013-09-27</date><risdate>2013</risdate><volume>19</volume><issue>40</issue><spage>13348</spage><epage>13354</epage><pages>13348-13354</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>The synthesis of four shape‐persistent macrocycles with three 1,8‐diazaanthracene units each is reported (2,3 a–3 c). For two of them single crystals could be obtained and the structures in the crystal be solved. The structures reveal that macrocycle 2 self‐dimerizes in the solid state; surprisingly it also forms a stable dimer in solution. The reason for this is seen in unusually efficient dispersion interactions as a consequence of the large contact areas in the dimer. All macrocycles are assessed as to their applicability in lateral polymerizations in the single crystal as well as in solution.
The perfect fit: Two shape‐persistent macrocycles such as A form a self‐assembled dimer in the single crystal which even under forcing conditions in solution cannot be made to dissociate into the single components.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24038419</pmid><doi>10.1002/chem.201301798</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry Contact crystal packing Crystal structure Dimers Dispersions macrocycles Macrocyclic compounds Molecular structure Polymerization shape-persistence Single crystals supramolecular self-dimerization Synthesis |
| title | Synthesis of Shape-Persistent Macrocycles with Three 1,8-Diazaanthracene Units and Their Packing in the Single Crystal |
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