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- W2138340115 endingPage "8917" @default.
- W2138340115 startingPage "8910" @default.
- W2138340115 abstract "Abstract Chimerical pyrene‐based dibenzo[7]helicene rac ‐ 1 and 2 H ‐pyran[7]helicene ( M , R , R )‐(−)‐ 2 , in which two pyrene subunits are fused to the [7]helicene/[7]heterohelicene scaffold, were synthesised by means of Ni 0 ‐ or Co I ‐mediated [2+2+2] cycloisomerisation of dipyrenyl‐acetylene‐derived triynes. Pyrene‐based dibenzo[7]helicene 1 was obtained in enantioenriched form by enantioselective cycloisomerisation under Ni 0 /QUINAP catalysis (57 % ee ) or in enantiopure form by racemate resolution by liquid chromatography on a chiral column. 1,3‐Allylic‐type strain‐controlled diastereoselective cycloisomerisation was employed in the synthesis of enantiopure ( M , R , R )‐(−)‐ 2 . Physicochemical properties of 1 and 2 encompassing the helicity assignment, stability to racemisation, X‐ray crystal structure, UV/Vis, experimental/calculated electronic circular dichroism and fluorescence spectra were studied. Accordingly, comparison of the X‐ray crystal structure of ( M , R , R )‐(−)‐ 2 with calculated structures (DFT: B3LYP/cc‐pVDZ, B97D/cc‐pVDZ) indicated that its helical backbone is slightly over‐flattened owing to intramolecular dispersion forces between tert ‐butylated pyrene subunits. Both 1 and 2 are fluorescent (with quantum yields in dichloromethane of Φ F =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 nm, respectively)." @default.
- W2138340115 created "2016-06-24" @default.
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- W2138340115 date "2015-04-29" @default.
- W2138340115 modified "2023-10-18" @default.
- W2138340115 title "Chimerical Pyrene-Based [7]Helicenes as Twisted Polycondensed Aromatics" @default.
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