Chimerical Pyrene-Based [7]Helicenes as Twisted Polycondensed Aromatics
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10296279" target="_blank" >RIV/00216208:11310/15:10296279 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/15:00444962
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201500826" target="_blank" >http://dx.doi.org/10.1002/chem.201500826</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201500826" target="_blank" >10.1002/chem.201500826</a>
Alternative languages
Result language
angličtina
Original language name
Chimerical Pyrene-Based [7]Helicenes as Twisted Polycondensed Aromatics
Original language description
Chimerical pyrene-based dibenzo[7]helicene rac-1 and 2H-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: B3
Czech name
—
Czech description
—
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—
Result continuities
Project
<a href="/en/project/GAP207%2F10%2F2207" target="_blank" >GAP207/10/2207: New Nonplanar Polyaromatic Systems of High Complexity: Their Synthesis and Properties</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
—
Volume of the periodical
21
Issue of the periodical within the volume
24
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
8910-8917
UT code for WoS article
000355287000036
EID of the result in the Scopus database
2-s2.0-84928619606