Enantiomerically Pure 5,13‐Dicyano‐9‐oxa[7]helicene: Synthesis and Study
Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4′‐biphenanthrene‐3,3′‐diol were resolved by physically separating their 1‐menthyl carbonate derivatives. In this work a mild method wa...
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| Veröffentlicht in: | European journal of organic chemistry 2018-10, Vol.2018 (39), p.5397-5405 |
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| container_issue | 39 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Gupta, Riddhi Cabreros, Trevor A. Muller, Gilles Bedekar, Ashutosh V. |
| description | Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4′‐biphenanthrene‐3,3′‐diol were resolved by physically separating their 1‐menthyl carbonate derivatives. In this work a mild method was developed to cleave ArOMe in presence of a cyano group. The optical rotation of atropisomeric diol, helicenes‐like compounds and the oxa[7]helicenes was observed to be in increasing order, while the molecules also showed good response to circularly polarized luminescence.
Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behaviour. The compounds show good response for circularly polarized luminescence. |
| doi_str_mv | 10.1002/ejoc.201800922 |
| format | Article |
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Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behaviour. The compounds show good response for circularly polarized luminescence.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201800922</identifier><identifier>PMID: 30853851</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Atropisomers ; Circular polarization ; Cyano groups ; Helicenes ; Isomers ; Luminescence ; Optical properties ; Optical rotation ; Photophysical properties</subject><ispartof>European journal of organic chemistry, 2018-10, Vol.2018 (39), p.5397-5405</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5342-2668d4c6b4d439f5020486af8071cd12a837d94b7a341ad1e32763262c15ffb33</citedby><cites>FETCH-LOGICAL-c5342-2668d4c6b4d439f5020486af8071cd12a837d94b7a341ad1e32763262c15ffb33</cites><orcidid>0000-0002-1104-6691 ; 0000-0001-7537-5390</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201800922$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201800922$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,315,782,786,887,1419,27931,27932,45581,45582</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30853851$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gupta, Riddhi</creatorcontrib><creatorcontrib>Cabreros, Trevor A.</creatorcontrib><creatorcontrib>Muller, Gilles</creatorcontrib><creatorcontrib>Bedekar, Ashutosh V.</creatorcontrib><title>Enantiomerically Pure 5,13‐Dicyano‐9‐oxa[7]helicene: Synthesis and Study</title><title>European journal of organic chemistry</title><addtitle>European J Org Chem</addtitle><description>Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4′‐biphenanthrene‐3,3′‐diol were resolved by physically separating their 1‐menthyl carbonate derivatives. In this work a mild method was developed to cleave ArOMe in presence of a cyano group. The optical rotation of atropisomeric diol, helicenes‐like compounds and the oxa[7]helicenes was observed to be in increasing order, while the molecules also showed good response to circularly polarized luminescence.
Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behaviour. The compounds show good response for circularly polarized luminescence.</description><subject>Atropisomers</subject><subject>Circular polarization</subject><subject>Cyano groups</subject><subject>Helicenes</subject><subject>Isomers</subject><subject>Luminescence</subject><subject>Optical properties</subject><subject>Optical rotation</subject><subject>Photophysical properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkc9LHDEUx0OxVGu99igDXjx01pcfk5n0IMh2aytSBS0UpIRsJtPNMpvYZKbt3PwT_Bv9Sxpdu1YvHkIevE8-vJcvQm8xjDAA2TNzr0cEcAUgCHmBNjAIkQMXsJZqRlmOBf22jl7HOIfEcI5foXUKVUGrAm-gLxOnXGf9wgSrVdsO2WkfTFa8w_Tm6vqD1YNyPlUiHf9HXZTfZ6a12jjzPjsbXDcz0cZMuTo76_p6eINeNqqNZuv-3kRfP07Ox5_y45PDz-OD41wXlJGccF7VTPMpqxkVTQEEWMVVU0GJdY2JqmhZCzYtFWVY1dhQUnJKONG4aJoppZtof-m97KcLU6d5uqBaeRnsQoVBemXl446zM_nD_5KcAWGiTILde0HwP3sTO7mwUZu2Vc74PkqCRfotRilJ6M4TdO774NJ6iSIMOJA7arSkdPAxBtOshsEgb6OSt1HJVVTpwfb_K6zwf9kkQCyB37Y1wzM6OTk6GT_I_wLigaHY</recordid><startdate>20181024</startdate><enddate>20181024</enddate><creator>Gupta, Riddhi</creator><creator>Cabreros, Trevor A.</creator><creator>Muller, Gilles</creator><creator>Bedekar, Ashutosh V.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-1104-6691</orcidid><orcidid>https://orcid.org/0000-0001-7537-5390</orcidid></search><sort><creationdate>20181024</creationdate><title>Enantiomerically Pure 5,13‐Dicyano‐9‐oxa[7]helicene: Synthesis and Study</title><author>Gupta, Riddhi ; Cabreros, Trevor A. ; Muller, Gilles ; Bedekar, Ashutosh V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5342-2668d4c6b4d439f5020486af8071cd12a837d94b7a341ad1e32763262c15ffb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Atropisomers</topic><topic>Circular polarization</topic><topic>Cyano groups</topic><topic>Helicenes</topic><topic>Isomers</topic><topic>Luminescence</topic><topic>Optical properties</topic><topic>Optical rotation</topic><topic>Photophysical properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gupta, Riddhi</creatorcontrib><creatorcontrib>Cabreros, Trevor A.</creatorcontrib><creatorcontrib>Muller, Gilles</creatorcontrib><creatorcontrib>Bedekar, Ashutosh V.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gupta, Riddhi</au><au>Cabreros, Trevor A.</au><au>Muller, Gilles</au><au>Bedekar, Ashutosh V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantiomerically Pure 5,13‐Dicyano‐9‐oxa[7]helicene: Synthesis and Study</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>European J Org Chem</addtitle><date>2018-10-24</date><risdate>2018</risdate><volume>2018</volume><issue>39</issue><spage>5397</spage><epage>5405</epage><pages>5397-5405</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4′‐biphenanthrene‐3,3′‐diol were resolved by physically separating their 1‐menthyl carbonate derivatives. In this work a mild method was developed to cleave ArOMe in presence of a cyano group. The optical rotation of atropisomeric diol, helicenes‐like compounds and the oxa[7]helicenes was observed to be in increasing order, while the molecules also showed good response to circularly polarized luminescence.
Optically pure dicyano oxa[7]helicenes and helicene‐like molecules have been prepared and investigated for their optical behaviour. The compounds show good response for circularly polarized luminescence.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30853851</pmid><doi>10.1002/ejoc.201800922</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-1104-6691</orcidid><orcidid>https://orcid.org/0000-0001-7537-5390</orcidid><oa>free_for_read</oa></addata></record> |
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| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Access via Wiley Online Library |
| subjects | Atropisomers Circular polarization Cyano groups Helicenes Isomers Luminescence Optical properties Optical rotation Photophysical properties |
| title | Enantiomerically Pure 5,13‐Dicyano‐9‐oxa[7]helicene: Synthesis and Study |
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