Cavitand-Based Pd-Pyridyl Coordination Capsules: Guest-Induced Homo- or Heterocapsule Selection and Applications of Homocapsules to the Protection of a Photosensitive Guest and Chiral Capsule Formation.

Autor: Nakamura M; Department of Chemistry Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan., Tsukamoto Y; Department of Chemistry Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan., Ueta T; Department of Chemistry Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan., Sei Y; Laboratory for Chemistry and Life Science Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan., Fukushima T; Laboratory for Chemistry and Life Science Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan., Yoza K; Bruker axs, 3-9-B Moriya, Kanagawa-ku, Yokohama, 221-0022, Japan., Kobayashi K; Department of Chemistry Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.; Research Institute of Green Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2020 Jul 16; Vol. 15 (14), pp. 2218-2230. Date of Electronic Publication: 2020 Jun 22.
DOI: 10.1002/asia.202000603
Abstrakt: A 2 : 4 mixture of tetrakis[4-(4-pyridyl)phenyl]cavitand (1) or tetrakis[4-(4-pyridyl)phenylethynyl]cavitand (2) and Pd(dppp)(OTf) 2 self-assembles into a homocapsule {1 2  ⋅ [Pd(dppp)] 4 } 8+  ⋅ (TfO - ) 8 (C1) or {2 2  ⋅ [Pd(dppp)] 4 } 8+  ⋅ (TfO - ) 8 (C2), respectively, through Pd-Npy coordination bonds. A 1 : 1 : 4 mixture of 1, 2, and Pd(dppp)(OTf) 2 produced a mixture of homocapsules C1, C2, and a heterocapsule {1 ⋅ 2 ⋅ [Pd(dppp)] 4 } 8+  ⋅ (TfO - ) 8 (C3) in a 1 : 1 : 0.98 mole ratio. Selective formation (self-sorting) of homocapsules C1 and C2 or heterocapsule C3 was controlled by guest-induced encapsulation under thermodynamic control. Applications of Pd-Npy coordination capsules with the use of 1 were demonstrated. Capsule C1 serves as a guard nanocontainer for trans-4,4'-diacetoxyazobenzene to protect against the trans-to-cis photoisomerization by encapsulation. A chiral capsule {1 2  ⋅ [Pd((R)-BINAP)] 4 } 8+  ⋅ (TfO - ) 8 (C5) was also constructed. Capsule C5 induces supramolecular chirality with respect to prochiral 2,2'-bis(alkoxycarbonyl)-4,4'-bis(1-propynyl)biphenyls by diastereomeric encapsulation through the asymmetric suppression of rotation around the axis of the prochiral biphenyl moiety.
(© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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