Trityl-Containing Alcohols—An Efficient Chirality Transmission Process from Inductor to the Stereodynamic Propeller and their Solid-State Structural Diversity

Górczyńska, Sylwia; Brzdonkiewicz, Aleksandra; Jelecki, Maciej; Czapik, Agnieszka; Stasiak, Bartosz; Kwit, Marcin

doi:10.3390/molecules25030707

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…The (H)O···H ortho C and C–H···π interactions stabilize the conformation of the second aryl ring, whereas the third one adjusts its conformation to the conformation of the remaining two that is stabilized by CH···π interactions. Thus, one would say that the structural information is transferred by the cascade process, which is, in general, similar to the recently proposed process of chirality transfer taking place in trityl-containing alcohols . In the cases where OH···O(R) hydrogen bonding is not present in the molecule, the (H)O···H ortho C interactions constitute the most important conformation-controlled factor.…”

Section: Resultssupporting

confidence: 62%

“…Thus, one would say that the structural information is transferred by the cascade process, which is, in general, similar to the recently proposed process of chirality transfer taking place in trityl-containing alcohols. 26 In the cases where OH···O(R) hydrogen bonding is not present in the molecule, the (H)O···H ortho C interactions constitute the most important conformation-controlled factor. The presence or absence of an OH···O(R) hydrogen bond in a given conformer reflects in the values of the α angle.…”

Section: Resultsmentioning

confidence: 99%

“…Slow evaporation of the solvents allowed to obtain crystals of ( R )- 3a , ( S )- 4a , ( R )- 4c , and ( S )- 6a (details on the crystallization of individual compounds can be found in the Supporting Information). Recently, it was found that some racemic trityl-containing compounds are prone to crystallize as solid solutions of enantiomers. , The trityl substituent can act as a supramolecular protecting group for the stereogenic center in triphenylacetyl acid derivatives, and the solid solution of enantiomers can be formed. The phenomenon of formation of solid solutions of enantiomers in organic crystals is not frequent; according to the literature data, it concerns less than 1% of racemic crystals .…”

Section: Resultsmentioning

confidence: 99%

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Dynamic Induction of Optical Activity in Triarylmethanols and Their Carbocations

2020

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A series of artificial triarylmethanols has been synthesized and studied toward the possibility of exhibiting an induced optical activity. The observed chiroptical response of these compounds resulted from the chiral conformation of a triarylmethyl core. The chirality induction from a permanent chirality element to the liable triarylmethyl core proceeds as a cooperative and cascade process. The OH···O(R) and/or (H)O···H ortho C hydrogen bond formation along with the C–H···π interactions seem to be the most important factors that control efficiency of the chirality induction. The position of chiral and methoxy electron-donating groups within a trityl skeleton affects the amplitude of observed Cotton effects and stability of the trityl carbocations. In the neutral environment, the most intense Cotton effects are observed for ortho -substituted derivatives, which undergo a rapid decomposition associated with the complete decay of ECD signals upon acidification. From all of the in situ generated stable carbocations, only two exhibit intense Cotton effects in the low energy region at around 450 nm. The formation of carbocations is reversible; after alkalization, the ions return to the original neutral forms. Unlike most triarylmethyl derivatives known so far, in the crystal, the triarylmethanol, para -substituted with the chiral moiety, shows a propensity for a solid-state sorting phenomenon.

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Section: Resultssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Dynamic Induction of Optical Activity in Triarylmethanols and Their Carbocations

2020

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Advances in Nanoclay‐Based Form Stable Phase Change Materials: A Review

Zhao

Zuo

Yang

2023

Adv Materials Technologies

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As the core material of thermal energy storage technology, phase change materials (PCM) suffer serious leakage problems and slow thermal conductivity in applications. Nanoclay with relatively high specific surface area, high thermal conductivity, and abundant pore structure can successfully compensate for the defects in PCM. However, the ability of nanoclay without further modification to encapsulate the PCM for the preparation of form stable phase change materials (FSPCM) and accelerate their heat transfer is limited. Nanoclay is classified into 1D, 2D, and 3D minerals based on their microscopic morphology. In this review, the specific surface and pore structure of three types of nanoclay and their thermal performance after loading with PCM are summarized and compared. Then, different mineral modification treatments, such as pretreatment, surface modification, structural modulation, and functional assembly, are summarized to investigate the enhancement of thermal performance in nanoclay‐based FSPCM. This review also summarizes the state‐of‐the‐art research progress of emerging nanoclay material‐based FSPCM. Finally, a summary of the traditional applications of mineral‐based FSPCM and an outlook on new applications are presented. This paper will help researchers to better understand the recent developments, performance enhancement strategies of nanoclay‐based FSPCM and to identify potential future research efforts.

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Inducing Propeller Chirality in Triaryl Boranes with Chiral Amines

Kemper

Reese

Engelage

et al. 2022

Chemistry A European J

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Stabilization of chiral propeller conformations in triaryl compounds is challenging due to generally low racemization barriers. Nonetheless, it was recently found that chiral conformational preferences can be induced to triaryl boranes by incorporating point‐chiral alkylether chains to the aryl blades and subsequently locking the structure with ammonia. A four‐point interaction, meaning that the cooperative effects of Lewis‐adduct formation and three hydrogen bonds, was proposed as stabilizing mechanism. Herein, it was shown that three such strong interactions suffice to introduce a preferential propeller handedness. Although DFT calculations predict no noteworthy preferences for either P‐ or M‐chiral propellers for some of the investigated triarylborane–amine adducts that were prepared with chiral primary amines, vibrational circular dichroism (VCD) spectroscopic characterizations revealed that there is indeed a measurable excess of one propeller handedness. Furthermore, the steric demand of the amine was found to play a key role in the induction process and especially in preventing blade rotations.

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Trityl-Containing Alcohols—An Efficient Chirality Transmission Process from Inductor to the Stereodynamic Propeller and their Solid-State Structural Diversity

Cited by 5 publications

References 28 publications

Dynamic Induction of Optical Activity in Triarylmethanols and Their Carbocations

Dynamic Induction of Optical Activity in Triarylmethanols and Their Carbocations

Advances in Nanoclay‐Based Form Stable Phase Change Materials: A Review

Inducing Propeller Chirality in Triaryl Boranes with Chiral Amines

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