{"id":21720,"date":"2019-12-22T12:30:02","date_gmt":"2019-12-22T12:30:02","guid":{"rendered":"https:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=21720"},"modified":"2019-12-22T12:30:02","modified_gmt":"2019-12-22T12:30:02","slug":"molecules-of-the-year-2019-twisty-tetracene","status":"publish","type":"post","link":"https:\/\/www.rzepa.net\/blog\/?p=21720","title":{"rendered":"Molecules of the year \u2013 2019: twisty tetracene."},"content":{"rendered":"
\n

All of the molecules in this year’s C&EN list<\/a> are fascinating in their very different ways. Here I take a look at the twisty tetracene (dodecaphenyltetracene) which is indeed very very twisty.[1]<\/a><\/span><\/p>\n

\"\"

Click on image to view 3D model<\/p><\/div>\n

\nUnfortunately, the authors point that the twisty-ness does not lead to a stable helical configuration at room temperatures and so separate enantiomers cannot be isolated. But its still worth speculating what the optical rotation of such a species might be if measured. An ωB97XD\/Def2-SVP\/SCRF=dichloromethane calculation (DOI: 10.14469\/hpc\/6527<\/a>) gives the following values:<\/p>\n

[α]589<\/sub> -11178°
\n[α]800<\/sub> -2310°<\/p>\n

Of course, mere helicity (however twisty) does not necessarily map to high optical rotation! This would be a nice molecule to 3D print<\/a> and sit on a coffee table for people to admire!<\/p>\n

References<\/h2>\n
  1. Y. Xiao, J.T. Mague, R.H. Schmehl, F.M. Haque, and R.A. Pascal, \"Dodecaphenyltetracene\", Angewandte Chemie International Edition<\/i>, vol. 58, pp. 2831-2833, 2019. https:\/\/doi.org\/10.1002\/anie.201812418<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> ","protected":false},"excerpt":{"rendered":"

    All of the molecules in this year’s C&EN list are fascinating in their very different ways. Here I take a look at the twisty tetracene (dodecaphenyltetracene) which is indeed very very twisty. Unfortunately, the authors point that the twisty-ness does not lead to a stable helical configuration at room temperatures and so separate enantiomers cannot […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[6],"tags":[1526],"class_list":["post-21720","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-interesting-chemistry"],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/p1gPyz-5Ek","jetpack_likes_enabled":true,"_links":{"self":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/21720","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=21720"}],"version-history":[{"count":0,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=\/wp\/v2\/posts\/21720\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=21720"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=21720"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rzepa.net\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=21720"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}