1180-60-5Relevant articles and documents
Lewis acid-catalyzed synthesis of dodecamethoxycalix[4]arene from 1,3,5-trimethoxybenzene and its conformational behavior and host-guest property
Ogoshi, Tomoki,Kitajima, Keisuke,Umeda, Kenji,Hiramitsu, Sachi,Kanai, Suguru,Fujinami, Shuhei,Yamagishi, Tada-aki,Nakamoto, Yoshiaki
, p. 10644 - 10649 (2009)
Lewis acid-catalyzed condensation of 1,2- and 1,3-dimethoxybenzenes with paraformaldehyde afforded an ortho-bridged cyclic trimer (1) and a meta-bridged cyclic tetramer (2), respectively. Furthermore, condensation of 1,3,5-trimethoxybenzene with paraformaldehyde in the presence of Lewis acid catalyst successfully rendered the first dodecamethoxy-substituted calix[4]arene (3) with high yield. From X-ray crystallography, it was found that 3 formed the partial cone conformation. The conformational behavior of 3 in the solution was investigated by variable temperature 1H NMR measurements. The partial cone structure observed in the solid state was retained in the solution at low temperatures. Furthermore, because of the slow conformational exchanges of 3 on the NMR time scale, bimodal conformational exchanges were found. The host-guest property of 3 with the electron accepting guest, tetracyanoethylene (TCNE) was examined by UV-Vis measurements, and the ability to associate with the 3-TCNE complex was three times higher than that of the 2-TCNE complex. The observation is due to the superior electron donating property and slow conformational exchanges of 3 compared with those of analogous 2.
Combaut et al.
, p. 1791 (1978)
Combant et al.
, p. 1699 (1978)
Silane catecholates: Versatile tools for self-assembled dynamic covalent bond chemistry
Kawakami, Yoshiteru,Ogishima, Tsuyoshi,Kawara, Tomoki,Yamauchi, Shota,Okamoto, Kazuhiko,Nikaido, Singo,Souma, Daiki,Jin, Ren-Hua,Kabe, Yoshio
, p. 6066 - 6069 (2019)
Shape-persistent macrocycles and 3D nanocages have been prepared in one-pot under MeCN-promoted dynamic covalent bond conditions starting from silane catecholates, whose structures were confirmed by X-ray crystallography. Cation-exchange reactions of macrocycles and nanocages were performed along with the encapsulation of ammonium ions within the cavity of an anionic macrocycle and a tetrahedral nanocage.
Miller,Gesner
, p. 3351,3352 (1965)
Hydrogen-bonded molecular capsules: Probing the role of water molecules in capsule formation in modified cyclotricatechylene
Illa, Giri Teja,Hazra, Sohan,Satha, Pardhasaradhi,Purohit, Chandra Shekhar
, p. 4759 - 4765 (2017/08/22)
Two new pyridine moiety-appended cavitands, CTC(Py)2(OH)2 and CTC(Py)3, were synthesized and characterized. The solid state structures of both cavitands were studied by single crystal X-ray diffraction. CTC(Py)2(OH)2 resulted in a hydrogen-bonded dimeric molecular capsule, entrapping two molecules of DMSO and intervening water molecules that formed hydrogen bonding to DMSO and CTC(Py)2(OH)2. When crystallized in the absence of water, it forms a 2D polymer by hydrogen bonding of pyridine nitrogen and phenolic hydrogen atoms. CTC(Py)3 forms no such capsule.
