Calixarene and hemicarcerand-like compounds obtained by self-assembly of 3-aminophenylboronic acid and salicylaldehyde derivatives

Use of 5-formylfuranboronic acid in the formation of bicyclic boronates with photophysical properties

“…In addition, the carbon signal base of the aldehyde group appears at d = 147.3 ppm before the opening ring reaction while it is observed in the range of d = 135.8 -142.3 ppm in the new products. 11 B NMR spectra analysis reveals that all systems showed broad signals between d = 1 and 4 ppm, in accordance with chemical shifts observed for boron atoms in a tetrahedral environment as described for related compounds [19][20][21].…”

“…Even if the whole molecular ion was only observed for methyl derivatives (6 and 7) at m/ z = 363, in all cases, a common peak corresponding to the molecular weight with the loss of a methanol molecule ([M-MeOH] + ) was observed as the pattern ion. The last statement has been observed for related compounds in which it is very common the loss of the OR group attached to the boron atom [20][21]. For all compounds, the experimental CHN elemental analysis are to related with the calculated values, except for carbon which showed values slightly different.…”

Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

“…The macrocyclic nature of the derivatives was evidenced by mass spectrometry, FAB + analysis reveals that the highest peak corresponds to the loss of a methoxy group from a trimeric compound [M‐OMe] + . This peak is characteristic in analogous calixlike derivatives …”

“…Using N‐donor ligands, coordinative or dative N–B bonds can be formed, given place to self‐assembled systems like macrocycles, polymeric, or cage compounds . Previously, we have described that boron macrocycles including boron‐nitrogen coordinative bonds are easily formed by reaction of salicylaldehyde derivatives with 3‐aminophenylboronic acid monohydrate . The reaction occurs in one‐pot synthesis leading to the formation of trimeric compounds in good yields.…”

Boron Macrocycles Based on Multicomponent Assemblies using (3‐Aminophenyl)boronic Acid and Pentaerythritol as Common Reagents; Molecular Receptors toward Lewis Bases

“…Previously, we have described the use of (3‐aminophenyl)boronic acid as a molecular tecton for the construction of a series of boronate structures including monomer,29 calixarene30–32 and hemicarcerand33,34 type compounds. Herein, we describe the use of a multicomponent reaction with a combination of (3‐aminophenyl)boronic acid, pentaerythritol, and mono‐ or dialdehyde derivatives to generate macrocyclic compounds.…”