Synthesis, Characterization, and Photophysical Properties of Triptycene-Based Chiral Organoboranes

Zhang, Songhe; Chen, Jinfa; Hu, Guo-Fei; Zhang, Niu; Wang, Nan; Yin, Xiaodong; Chen, Pangkuan

doi:10.1021/acs.organomet.1c00447

Cited by 3 publications

(1 citation statement)

References 42 publications

(35 reference statements)

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“…The field of chiral triptycene-containing supramolecular systems is "opening up" as researchers exploit their unique properties to develop new chiral materials and supramolecules. Selected chiral triptycenes have recently been successfully incorporated into nanostructures as metallamacrocycles, π-conjugated oligomers or polymers, and supramolecular receptors [18][19][20][21][22][23][24]; the applications of chiral triptycenes are still relatively unexplored, due to the lack of useful strategies to obtain these synthons in enantiopure form on a large scale. Potential strategies for obtaining enantiopure chiral triptycenes are crystallization of diastereomeric salts, enantioselective synthesis, chiral HPLC, and resolution with chiral auxiliaries.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,6-Diaminotriptycene Conjugates with Chiral Auxiliaries: Towards the Scalable Resolution of Crucial Triptycene Intermediates

Preda,

Casali,

Porta

et al. 2024

Symmetry

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Triptycenes are tridimensional molecular scaffolds with interesting properties for applications in materials science: molecular rigidity and preorganization, tailorable chromophores, and, with an appropriate substitution pattern, chirality. The separation of the two enantiomers of chiral triptycenes has been the subject of increasing interest in recent years, with limited success. Here, we report the synthesis and characterization of a series of new organic compounds, in which a chiral triptycene scaffold, derivatized in the 2 and 6 positions with amino groups, has been functionalized with different enantiopure chiral auxiliaries, forming diastereoisomeric couples. The properties of such compounds, in terms of the optimization of their chromatographic separation, are elucidated with the aid of computational calculations of preferred conformations and molecular polarities.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2,6-Diaminotriptycene Conjugates with Chiral Auxiliaries: Towards the Scalable Resolution of Crucial Triptycene Intermediates

Preda,

Casali,

Porta

et al. 2024

Symmetry

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Design and Synthesis of New Type of Macrocyclic Architectures Used for Optoelectronic Materials and Supramolecular Chemistry

Jia

Chen

2023

Chemistry A European J

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Supramolecular chemistry has received much attention for decades. Macrocyclic architectures as representative receptors play a vital role in supramolecular chemistry and are applied in many fields such as supramolecular assembly and host‐guest recognition. However, the classical macrocycles generally lack functional groups in the scaffolds, which limit their further applications, especially in optoelectronic materials. Therefore, developing new design principle is not only essential to better understand macrocyclic chemistry and the supramolecular behaviors, but also further expand their applications in many research fields. In recent years, the doping compounds with main‐group heteroatoms (B, N, S, O, P) into the carbon‐based π‐conjugated macrocycles offered a new strategy to build macrocyclic architectures with unique optoelectronic properties. In particular, the energy gaps and redox behavior can be effectively tuned by incorporating heteroatoms into the macrocyclic scaffolds. In this Minireview, we briefly summarize the design and synthesis of new macrocycles, and further discuss the related applications in optoelectronic materials and supramolecular chemistry.

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Applying the B/N Lewis Pair Approach to Access Fusion-Expanded Binaphthyl-Based Chiral Analogues

et al. 2022

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We herein describe the synthesis of two axially chiral systems (HBN and BBN) by the incorporation of B centers into binaphthyl derivatives (HPy and BPy). Heteroatom-doped chiral polycyclic aromatic hydrocarbons were thus formed by fusion of the azaboroles to binaphthyls with the formation of B−N dative bonds. The resulting B−N Lewis pairs that serve as attractive fluorophores enabled modulation of the chiroptical properties both in solution and in the solid state.

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Synthesis, Characterization, and Photophysical Properties of Triptycene-Based Chiral Organoboranes

Cited by 3 publications

References 42 publications

Synthesis of 2,6-Diaminotriptycene Conjugates with Chiral Auxiliaries: Towards the Scalable Resolution of Crucial Triptycene Intermediates

Synthesis of 2,6-Diaminotriptycene Conjugates with Chiral Auxiliaries: Towards the Scalable Resolution of Crucial Triptycene Intermediates

Design and Synthesis of New Type of Macrocyclic Architectures Used for Optoelectronic Materials and Supramolecular Chemistry

Applying the B/N Lewis Pair Approach to Access Fusion-Expanded Binaphthyl-Based Chiral Analogues

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