{"id":399,"date":"2009-04-28T10:22:09","date_gmt":"2009-04-28T09:22:09","guid":{"rendered":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399"},"modified":"2011-07-07T06:07:50","modified_gmt":"2011-07-07T06:07:50","slug":"the-chirality-of-lemniscular-octaphyrins","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399","title":{"rendered":"The Chirality of Lemniscular Octaphyrins"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"399\">\n<p>In the <a href=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=363\" target=\"new\">previous post<\/a>, \u00a0it was noted that \u00a0M\u00f6bius annulenes are intrinsically chiral, and should therefore in principle be capable of resolution into enantiomers. The synthesis of such an annulene by  Herges and co-workers was a racemic one; no attempt was reported at any resolution into such enantiomers.  Here theory can help, since calculating the  optical rotation [\u03b1]D  is nowadays a relatively reliable process for rigid molecules. The rotation (in \u00b0) calculated for that  M\u00f6bius annulene was relatively large compared to that normally measured for most small molecules.<\/p>\n<p>Recently,  quite a number of  cyclopolypyrroles, more commonly called phyrins, have been reported. The conventional number of pyrrole rings in many biological systems is of course four (chlorophyll, haemoglobin, etc),  but these extended porphyrins can have anywhere between five and sixteen such rings comprising a larger macrocycle.  For those with six-eight such rings, a commonly adopted geometric motif is found to be a  <em>figure-eight<\/em>, or more properly a <em>lemniscular<\/em> one. Such shapes have recently  (<a href=\"http:\/\/dx.doi.org\/10.1021\/ol703129z\" target=\"new\">10.1021\/ol703129z<\/a>) been recognized as also being  M\u00f6bius systems, albeit this time with two half twists in the  \u03c0-electron cycle rather than just the single twist synthesized by  Herges. As such, they also follow a simple electronic selection rule,  being <strong>aromatic<\/strong> if  4n+2 \u03c0-electrons circulate around the ring.<\/p>\n<p>One such molecule is shown below (<a href=\"http:\/\/dx.doi.org\/10.1039\/b502327k\" target=\"new\">10.1039\/b502327k<\/a>), albeit with four of the pyrroles replaced by a thiophene ring.<\/p>\n<p><div id=\"attachment_401\" style=\"width: 451px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" aria-describedby=\"caption-attachment-401\" class=\"size-full wp-image-401\" title=\"qarfar\" onclick=\"jmolInitialize('..\/Jmol\/');jmolSetAppletColor('white');jmolApplet([450,450],'load wp-content\/uploads\/2009\/04\/qarfar-126.jvxl;zoom 10;isosurface &quot;&quot; translucent;moveto 4 0 2 0 90 120;spin 5;');\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg\" alt=\"A 34-Octaphyrin. Click to see molecule\" width=\"441\" height=\"246\" \/><p id=\"caption-attachment-401\" class=\"wp-caption-text\">A 34-Octaphyrin. Click for 3D.<\/p><\/div>Just as with the Herges syntheses, most of these phyrins are also made as racemates. There appears to be only one report of  such octaphyrin actually being separated into  enantiomers (<a href=\"http:\/\/dx.doi.org\/10.1002\/(SICI)1521-3773(19991216)38:24&lt;3650::AID-ANIE3650&gt;3.0.CO;2-F\" target=\"new\">10.1002\/(SICI)1521-3773(19991216)38:24&lt;3650::AID-ANIE3650&gt;3.0.CO;2-F<\/a>) but no optical rotation could be measured due to its intense colour (in other words, so much light is absorbed by the system that too little remains to measure its rotation).  So no-one knows what the magnitudes of the optical rotation values for these figure-eight or lemniscular molecules actually are.<\/p>\n<p>Here again, theory can come to the rescue.  The octaphyrin shown above for example (simplified such that  Ar=H), [\u03b1]D  has the stupendous value of -25517\u00b0 (See <a href=\"http:\/\/hdl.handle.net\/10042\/to-2185\" target=\"new\">10042\/to-2185<\/a>).  Values above  10,000 are common for this type of molecule!  So these relatively small and simple class of molecules are currently easily the record holders for the size of their optical rotations.  OK, the latter are merely predictions,  but it certainly should serve as an encouragement for experimental measurements of this property.<\/p>\n<p>Oh, by the way, if you click on the graphic above, you will get to see a molecular orbital calculated for the molecule.  It is the most stable of the  \u03c0-type of  MOs, and shows the characteristic features of the lemniscate, namely the  \u03c0-electrons take the form of a torus link (<a href=\"http:\/\/dx.doi.org\/10.1039\/b810301a\" target=\"new\">10.1039\/b810301a<\/a>).<\/p>\n<!-- kcite active, but no citations found -->\n<\/div> <!-- kcite-section 399 -->","protected":false},"excerpt":{"rendered":"<p>In the previous post, \u00a0it was noted that \u00a0M\u00f6bius annulenes are intrinsically chiral, and should therefore in principle be capable of resolution into enantiomers. The synthesis of such an annulene by Herges and co-workers was a racemic one; no attempt was reported at any resolution into such enantiomers. Here theory can help, since calculating the [&hellip;]<\/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,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":false,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[4],"tags":[58,575,2648],"ppma_author":[2661],"class_list":["post-399","post","type-post","status-publish","format-standard","hentry","category-interesting-chemistry","tag-biological-systems","tag-chiroptical","tag-interesting-chemistry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The Chirality of Lemniscular Octaphyrins - Henry Rzepa&#039;s Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The Chirality of Lemniscular Octaphyrins - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"In the previous post, \u00a0it was noted that \u00a0M\u00f6bius annulenes are intrinsically chiral, and should therefore in principle be capable of resolution into enantiomers. The synthesis of such an annulene by Herges and co-workers was a racemic one; no attempt was reported at any resolution into such enantiomers. 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The synthesis of such an annulene by Herges and co-workers was a racemic one; no attempt was reported at any resolution into such enantiomers. Here theory can help, since calculating the [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2009-04-28T09:22:09+00:00","article_modified_time":"2011-07-07T06:07:50+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"2 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"The Chirality of Lemniscular Octaphyrins","datePublished":"2009-04-28T09:22:09+00:00","dateModified":"2011-07-07T06:07:50+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399"},"wordCount":468,"commentCount":1,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg","keywords":["biological systems","chiroptical","Interesting chemistry"],"articleSection":["Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399","name":"The Chirality of Lemniscular Octaphyrins - Henry Rzepa&#039;s Blog","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#primaryimage"},"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg","datePublished":"2009-04-28T09:22:09+00:00","dateModified":"2011-07-07T06:07:50+00:00","author":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"breadcrumb":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#breadcrumb"},"inLanguage":"en-GB","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399"]}]},{"@type":"ImageObject","inLanguage":"en-GB","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#primaryimage","url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg","contentUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/qarfar.jpg"},{"@type":"BreadcrumbList","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=399#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog"},{"@type":"ListItem","position":2,"name":"The Chirality of Lemniscular Octaphyrins"}]},{"@type":"WebSite","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#website","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/","name":"Henry Rzepa&#039;s Blog","description":"Chemistry with a twist","potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-GB"},{"@type":"Person","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281","name":"Henry Rzepa","image":{"@type":"ImageObject","inLanguage":"en-GB","@id":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g370be3a7397865e4fd161aefeb0a5a85","url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","caption":"Henry Rzepa"},"description":"Henry Rzepa is Emeritus Professor of Computational Chemistry at Imperial College London.","sameAs":["https:\/\/orcid.org\/0000-0002-8635-8390"],"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?author=1"}]}},"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/pDef7-6r","jetpack-related-posts":[{"id":363,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=363","url_meta":{"origin":399,"position":0},"title":"The chirality of  M\u00f6bius annulenes","author":"Henry Rzepa","date":"April 22, 2009","format":false,"excerpt":"Much like climbing Mt. Everest because its there, \u00a0some hypothetical molecules are just too tantalizing for chemists to resist attempting a synthesis. Thus in 1964, Edgar Heilbronner \u00a0speculated on whether a conjugated annulene ring might be twistable into a \u00a0M\u00f6bius strip. It was essentially a fun thing to try to\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"The 16-annulene synthesized by Herges and his team.","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2009\/04\/herges.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":24503,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=24503","url_meta":{"origin":399,"position":1},"title":"Molecule of the year 2021: Infinitene.","author":"Henry Rzepa","date":"December 16, 2021","format":false,"excerpt":"The annual \"molecule of the year\" results for 2021 are now available ... and the winner is Infinitene., This is a benzocirculene in the form of a figure eight loop (the infinity symbol), a shape which is also called a lemniscate after the mathematical (2D) function due to Bernoulli. The\u2026","rel":"","context":"In &quot;Chiroptics&quot;","block_context":{"text":"Chiroptics","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2644"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2021\/12\/infinitene.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":9322,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9322","url_meta":{"origin":399,"position":2},"title":"Anapolar ring currents: a [144]-Annulene.","author":"Henry Rzepa","date":"February 1, 2013","format":false,"excerpt":"This is a recently published (hypothetical) molecule which has such unusual properties that I cannot resist sharing it with you. It is an annulene with 144 all-cis CH groups, being a (very) much larger cousin of (also hypothetical) systems mooted in 2009,. One fascinating novel aspect of Berger's work is\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"A 144-carbon annulene. Click for  3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/02\/C144.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":21720,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=21720","url_meta":{"origin":399,"position":3},"title":"Molecules of the year \u2013 2019: twisty tetracene.","author":"Henry Rzepa","date":"December 22, 2019","format":false,"excerpt":"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\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2019\/12\/tetracene-1024x726.jpg?resize=350%2C200&ssl=1","width":350,"height":200},"classes":[]},{"id":9512,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=9512","url_meta":{"origin":399,"position":4},"title":"Helically conjugated molecules. A follow-up to [144]-annulene.","author":"Henry Rzepa","date":"February 12, 2013","format":false,"excerpt":"An extensive discussion developed regarding my post on a fascinating helical [144]-annulene. Topics included the nature of the ring current sustained by the\u00a0\u03c0-electrons and in particular the bond-length alternation around the periphery and whether this should alter if the electron count were to be changed to that of a 4n+2\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"SELQUW. Click for 3D.","src":"https:\/\/i0.wp.com\/www.ch.imperial.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2013\/02\/SELQUW.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":30975,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30975","url_meta":{"origin":399,"position":5},"title":"The first &#8220;half-M\u00f6bius&#8221; molecule: A question about its twist?","author":"Henry Rzepa","date":"March 13, 2026","format":false,"excerpt":"The recent report of what is termed a \"half-M\u00f6bius\" molecule is generating a lot of excitement. It has its origins in a project to make odd-numbered cyclocarbons on STM (scanning tunnelling microscope) surfaces. I had discussed even-numbered cyclocarbons in another post, where I also happened to include several odd-numbered examples,\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]}],"jetpack_likes_enabled":false,"authors":[{"term_id":2661,"user_id":1,"is_guest":0,"slug":"admin","display_name":"Henry Rzepa","avatar_url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/399","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=399"}],"version-history":[{"count":0,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/399\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=399"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=399"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=399"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=399"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}