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Geländer Molecules with Orthogonal Joints: Synthesis of Macrocyclic Dimers.

Geländer Molecules with Orthogonal Joints: Synthesis of Macrocyclic Dimers.

Authors :
D'Addio A
Malinčik J
Fuhr O
Fenske D
Häussinger D
Mayor M
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2022 Oct 07; Vol. 28 (56), pp. e202201678. Date of Electronic Publication: 2022 Aug 18.
Publication Year :
2022

Abstract

Orthogonal joints, understood as connections with an angle of 90°, were introduced in the design of the "Geländer" model compounds 1 and 2. The banister, consisting of a conjugated carbazole dimer linked by either 1,3-butadiyne (2) or a single thiophene (1), wraps around an axis composed of a phthalimide dimer due to the dimensional mismatch of both subunits, which are interconnected by phenylene rungs. The "Geländer" structure was assembled from a monomer comprising the 1,4-diaminobenzene rung with one amino substituent as part of a 4-bromo phthalimide subunit forming the orthogonal junction to the axis, and the other as part of a masked 2-ethynyl carbazole as orthogonal joint to the banister. The macrocycle was obtained by two sequential homocoupling steps. A first dimerization by a reductive homocoupling assembled the axis, while an oxidative acetylene coupling served as ring-closing reaction. The formed butadiyne was further derivatized to a thiophene, rendering all carbons of the model compound sp <superscript>2</superscript> hybridized. Both helical structures were fully characterized and chirally resolved. Assignment of the enantiomers was achieved by simulation of chiroptical properties and enantiopure synthesis.<br /> (© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3765
Volume :
28
Issue :
56
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
35856176
Full Text :
https://doi.org/10.1002/chem.202201678