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Pyrene\u2010based dibenzo[7]helicene <jats:bold>1<\/jats:bold> was obtained in enantioenriched form by enantioselective cycloisomerisation under Ni<jats:sup>0<\/jats:sup>\/QUINAP catalysis (57\u2009% <jats:italic>ee<\/jats:italic>) or in enantiopure form by racemate resolution by liquid chromatography on a chiral column. 1,3\u2010Allylic\u2010type strain\u2010controlled diastereoselective cycloisomerisation was employed in the synthesis of enantiopure (<jats:italic>M<\/jats:italic>,<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010<jats:bold>2<\/jats:bold>. Physicochemical properties of <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> encompassing the helicity assignment, stability to racemisation, X\u2010ray crystal structure, UV\/Vis, experimental\/calculated electronic circular dichroism and fluorescence spectra were studied. Accordingly, comparison of the X\u2010ray crystal structure of (<jats:italic>M<\/jats:italic>,<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010<jats:bold>2<\/jats:bold> with calculated structures (DFT: B3LYP\/cc\u2010pVDZ, B97D\/cc\u2010pVDZ) indicated that its helical backbone is slightly over\u2010flattened owing to intramolecular dispersion forces between <jats:italic>tert<\/jats:italic>\u2010butylated pyrene subunits. Both <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> are fluorescent (with quantum yields in dichloromethane of <jats:italic>\u03a6<\/jats:italic><jats:sub>F<\/jats:sub>=0.10 and 0.17, respectively) and are suggested to form intramolecular excimer states upon excitation, which are remarkably stabilised and exhibit large Stokes shifts (296 and 203\u2005nm, respectively).<\/jats:p>","DOI":"10.1002\/chem.201500826","type":"journal-article","created":{"date-parts":[[2015,4,29]],"date-time":"2015-04-29T16:27:21Z","timestamp":1430324841000},"page":"8910-8917","source":"Crossref","is-referenced-by-count":88,"title":["Chimerical Pyrene\u2010Based [7]Helicenes as Twisted Polycondensed Aromatics"],"prefix":"10.1002","volume":"21","author":[{"given":"Michal","family":"Buchta","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159\u00ed","family":"Ryb\u00e1\u010dek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrej","family":"Jan\u010da\u0159\u00edk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amit A.","family":"Kudale","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Milo\u0161","family":"Bud\u011b\u0161\u00ednsk\u00fd","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jana Vacek","family":"Chocholou\u0161ov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaroslav","family":"Vacek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Bedn\u00e1rov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivana","family":"C\u00edsa\u0159ov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Graham J.","family":"Bodwell","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivo","family":"Star\u00fd","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irena G.","family":"Star\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,4,29]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For recent and early reviews see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35154D"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35111K"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35134J"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2OB27108G"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200087r"},{"key":"e_1_2_6_7_2","first-page":"885","volume-title":"Science of Synthesis, Vol.\u200545b","author":"Star\u00e1 I. 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