Tribenzotriquinacene Fused Dimers (“Fusodimers”)—Synthesis and Host–Guest Properties
- 1Department of Chemistry The Chinese University of Hong Kong Shatin New Territories Hong Kong
- 2State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University Lanzhou P.R. China
- 3Department of Chemistry and Center for Molecular Materials (CM2 ) Bielefeld University Bielefeld Germany
Abstract
The synthesis and structural properties of two stereoisomeric tribenzotriquinacene (TBTQ) derivatives, syn‐4 and anti‐4, in which two rigid TBTQ bowls share a common benzene ring, are described. Owing to the orthogonal orientation of the three indane wings in each of the TBTQ units, four veratrole rings point either at right angles or parallel into the 3‐space. In contrast to the convex‐concave anti‐isomer, the biconcave fusodimer syn‐4 was found to host C60 and C70 fullerenes as 1:1 complexes both in solution and in the solid state, as shown by 1H NMR spectroscopy and x‐ray crystallography. Complexation‐induced chemical shift (CIS) measurements gave similar binding constants, K a = 382 (± 4) for syn‐4⊂C60 and K a = 410 (± 8) M− 1 for syn‐4⊂C70. Structural details of the torsion and widening of the formally C 2v‐symmetric host skeleton upon embedding of the fullerenes into the deep biconcave molecular surface of syn‐4 were determined along with intermolecular peculiarities of the solid‐state complexes.
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BibTeX
@article{ng2026tribenzotriquinacene,
title = {{Tribenzotriquinacene Fused Dimers (“Fusodimers”)—Synthesis and Host–Guest Properties}},
author = {Chun‐Fai Ng and Lisi He and Yin‐Ying Cheung and Xiao‐Ping Cao and Dietmar Kuck and Hak‐Fun Chow},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
year = {2026},
month = aug,
doi = {10.1002/chem.71574},
url = {https://doi.org/10.1002/chem.71574},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Tribenzotriquinacene Fused Dimers (“Fusodimers”)—Synthesis and Host–Guest Properties
AU - Chun‐Fai Ng
AU - Lisi He
AU - Yin‐Ying Cheung
AU - Xiao‐Ping Cao
AU - Dietmar Kuck
AU - Hak‐Fun Chow
PY - 2026
DA - 2026/08/17
JO - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO - 10.1002/chem.71574
UR - https://doi.org/10.1002/chem.71574
AB - The synthesis and structural properties of two stereoisomeric tribenzotriquinacene (TBTQ) derivatives, syn‐4 and anti‐4, in which two rigid TBTQ bowls share a common benzene ring, are described. Owing to the orthogonal orientation of the three indane wings in each of the TBTQ units, four veratrole rings point either at right angles or parallel into the 3‐space. In contrast to the convex‐concave anti‐isomer, the biconcave fusodimer syn‐4 was found to host C60 and C70 fullerenes as 1:1 complexes both in solution and in the solid state, as shown by 1H NMR spectroscopy and x‐ray crystallography. Complexation‐induced chemical shift (CIS) measurements gave similar binding constants, K a = 382 (± 4) for syn‐4⊂C60 and K a = 410 (± 8) M− 1 for syn‐4⊂C70. Structural details of the torsion and widening of the formally C 2v‐symmetric host skeleton upon embedding of the fullerenes into the deep biconcave molecular surface of syn‐4 were determined along with intermolecular peculiarities of the solid‐state complexes.
SN - 0947-6539
SN - 1521-3765
ER -