Molecular Waterwheel (Noria) from a Simple Condensation of Resorcinol and an Alkanedial

Abstract

A wheel surprise: Reaction of resorcinol and 1,5‐pentanedial in ethanol at 80 °C for 48 h in the presence of HCl surprisingly afforded a soluble cyclic oligomer in high yield (83 %) under thermodynamic control. Single‐crystal X‐ray analysis revealed a waterwheel‐like structure with a large hydrophobic hole through the center (see picture). A carboxylic ester derivative of the compound was shown to be highly selective for Rb+ ions.

Study on resist performance of chemically amplified molecular resists based on cyclic oligomers

“…Figure 1 shows Resists 1-4, which were based on noria. 6 Resists 1 and 2 were prepared from noria derivatives with pendant adamantyl ester (AD) and cyclohexyl 2-propyl ether moieties, whose degrees of protecting groups (DP) were 40 and 23%, respectively.…”

“…Recently, Kudo and co-workers succeeded in the synthesis of a new ladder cyclic oligomer "noria" (water wheel in Latin) 6 and reported the synthesis and photochemical reactivity of noria derivatives containing t-butoxycarbonyl groups, 7,8 t-butylester groups, 9 acetal groups, 10,11 and adamantyl ester groups. [12][13][14][15] It was found that these noria derivatives had high photo-reactivity and produced clear line and space patterns with resolutions of 50-70 nm using an EB exposure tool and 26 nm using EUV exposure tool, respectively.…”

Study on Resist Performance of Noria Derivatives Modified with Various Protection Ratios of Acetal Moieties by means of Extreme Ultraviolet Irradiation

“…Recently, Kudo and coworkers have succeeded in the synthesis of a new ladder cyclic oligomer "noria" (water wheel in Latin) [13] and reported the synthesis and photochemical reactivity of noria derivatives containing t-butoxycarbonyl groups [14,15], t-butylester groups [16], acetal groups [17,18], and adamantyl ester groups [19][20][21][22][23]. It was found that these noria derivatives have high photoreactivity and produce clear line and space patterns with resolutions of 50-70 nm using an EB exposure tool and 26 nm using an EUV exposure tool [15][16][17][18][19][20][21][22][23].…”

Synthesis and Resist Properties of Hyperbranched Polyacetals

“…To overcome this problem, the development of superior photo-resist materials have been required. We also have been investigated to offer higher resolution resist pattern based on ladder cyclic oligomer "noria" (noria = water wheel in Latin) [3]. The synthesis, physical properties, and patterning properties of noria derivatives with pendant t-butyl ester groups [4], t-butyloxycarbonyl groups [5], adamantyl ester groups [6 -8], and cyclohexyl acetal moieties [9], and oxetanyl groups [10] using EB and EUV exposure system.…”