Monolayers of triaroylbenzene derivatives

Dighe, Mayuri K.; Dover, Frank J.; Stine, Keith J.; Pigge, F. Christopher

doi:10.1016/j.tsf.2007.09.025

Cited by 2 publications

(1 citation statement)

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“…[13] The tri(pcyanophenyl) derivative was used as a ligand for a coordina-tion polymer, [14] and tri(p-octyloxybenzoyl)benzene has been fabricated into a monolayer. [15] When attached with poly-A C H T U N G T R E N N U N G (oxyethylene) units, the resulting crownophanes crystallized as inclusion solids. [16] Moreover, the propiolyl group has been introduced into a calixarene moiety, which was cyclotrimerized to form tri-and pentacalixarenes that served as host molecules for amines, polyamines, and C 60 .…”

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One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

Tanaka

Nakamura

Iwado

et al. 2010

Chemistry A European J

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Cyclotrimerization of 1-phenyl-2-propyn-1-one in pressurized hot water gave 1,3,5-tribenzoylbenzene in one pot in 65 % yield after 7 min at 200 °C, or in 74 % yield after 60 min at 150 °C. The reaction did not take place in the absence of water, and added base promoted the reaction at 250 °C, suggesting a mechanism of three-consecutive Michael addition reactions. The reaction rates increased with temperature, but the yield of 1,3,5-tribenzoylbenzene decreased at the expense of formation of acetophenone as a side product at higher temperatures. p-Methyl and p-chloro-substituents on the phenyl ring retarded and enhanced the reaction, respectively. A mechanism involving the enol of benzoylacetaldehyde at a branching point of the pathway leading to 1,3,5-tribenzoylbenzene and acetophenone was suggested.

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confidence: 99%

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

Tanaka

Nakamura

Iwado

et al. 2010

Chemistry A European J

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Brewster Angle Microscopy

Stine

2012

Supramolecular Chemistry

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Brewster angle microscopy (BAM) is the technique of choice for imaging monolayers of supramolecular systems at the water–air interface. BAM is based on the optical principle of the Brewster angle, in which p ‐polarized light incident on the water surface at the Brewster angle is nearly completely extinguished. The presence of a monolayer violates this condition and provides the basis for imaging. BAM is a general method for imaging either spread or adsorbed monolayers. BAM can be applied to study phase transitions, characterize domain microstructure, study phase separation in mixed monolayers, follow changes due to complex formation, and observe collapse or multilayer formation. The method is also sensitive to the presence of optical anisotropy in monolayer films due to variations in molecular orientation. BAM has been applied to monolayers of a range of macrocyclic compounds, especially calixarene and cyclodextrin derivatives. BAM has been applied to study chiral phase separation in monolayers of chiral amphiphiles. It is possible to apply BAM in a quantitative manner to estimate variations in monolayer thickness.

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Monolayers of triaroylbenzene derivatives

Cited by 2 publications

References 39 publications

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

One‐Pot Synthesis of 1,3,5‐Tribenzoylbenzenes by Three Consecutive Michael Addition Reactions of 1‐Phenyl‐2‐propyn‐1‐ones in Pressurized Hot Water in the Absence of Added Catalysts

Brewster Angle Microscopy

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