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Geländer Molecules with Orthogonal Joints: Synthesis of Macrocyclic Dimers.
Geländer Molecules with Orthogonal Joints: Synthesis of Macrocyclic Dimers.
- 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