AIE‐Active Chiral [3]Rotaxanes with Switchable Circularly Polarized Luminescence

Li, Wei‐Jian; Gu, Qingyi; Wang, Xu‐Qing; Zhang, Dan‐Yang; Wang, Yu‐Te; He, Xiao; Wang, Wei; Yang, Hai‐Bo

doi:10.1002/ange.202100934

Cited by 30 publications

(4 citation statements)

References 115 publications

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“…With such design strategy in mind, in this study, pentafluorophenyl ester moiety 43 was introduced as exchangeable stoppers. In addition, considering the unique planar chirality of pillar [5]arene [44][45][46] , its host-guest complex with neutral alkyl chain was employed as the rotaxane moiety for the synthesis of chiral rotaxanes. The reaction of sebacoyl chloride with pentafluorophenol in the presence of an excess of diethyoxypillar [5]arene (DEP [5]A) and Et3N in CHCl3 afforded the desired [2]rotaxane precursor 1 (Supplementary Scheme S2).…”

Section: General Design Strategy and The Preparation Of Key [2]rotaxa...mentioning

confidence: 99%

Sequence Matters: Precise Synthesis of Hetero[3]rotaxane Isomers with Sequence-dependent Chemical Reactivity and Circularly Polarized Luminescence

Peng

Jia

Wang

et al. 2023

Preprint

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Sequence isomerism plays fundamental roles in the encoding of biological information and in tuning material performance, but engineering sequences and elucidating their effects remain a major and largely unmet challenge in synthetic chemistry. Herein, We develop a novel wheel assembling approach aiming at the precise sequence control of hetero[3]rotaxanes, a typical family of mechanically interlocked molecules. Based on a key [2]rotaxane precursor with exchangeable pentafluorophenyl ester stoppers, We successfully synthesized both sequence isomers of diverse hetero[3]rotaxanes. Moreover, taking advantage of the chirality retention along with the wheel assembling process, corresponding sequence isomers of chiral functionalized hetero[3]rotaxanes were further precisely synthesized. Impressively, these hetero[3]rotaxanes revealed remarkable sequence-dependent chemical reactivity and circularly polarized luminescence, highlighting fantastic sequence effects. This proof-of-concept study lays the foundation for the investigations on the structure-property relationships of heterorotaxanes, which would further direct the rational design and precise synthesis of sequence-defined heterorotaxanes with desired properties for practical use.

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Section: General Design Strategy and The Preparation Of Key [2]rotaxa...mentioning

confidence: 99%

Sequence Matters: Precise Synthesis of Hetero[3]rotaxane Isomers with Sequence-dependent Chemical Reactivity and Circularly Polarized Luminescence

Peng

Jia

Wang

et al. 2023

Preprint

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“…Herein, based on our on-going research interests in pillar [5]arene-based mechanically interlocked molecules (MIMs), especially rotaxane dendrimers [33][34][35][36][37] and CPL-active chiral rotaxanes, [38][39][40] we assumed that the asymmetric Sonogashira coupling reaction [41][42] would be a suitable choice for the synthesis of novel planar chiral pillar [5]arenes. On the one hand, the further extension of the conjugated skeletons of the resultant products would endow them with attractive tunable chiroptical properties, making them promising platforms as novel chiral luminescent materials for practical applications.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Synthesis of Planar Chiral Pillar[5]arenes via Asymmetric Sonogashira Coupling

Zhou,

Zhang,

Song

et al. 2024

Preprint

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As a novel type of macrocycles with attractive planar chirality, pillar[5]arenes have gained increasing research interest over the past decades, enabling their widespread applications in diverse fields such as porous materials, molecular machines, and chiral luminescence materials. However, the catalytic methodology towards the enantioselective synthesis of planar chiral pillar[5]arenes remains elusive. Here we report a novel method for the enantioselective synthesis of planar chiral pillar[5]arenes via asymmetric Sonogashira coupling, giving access to a wide range of highly functionalized planar chiral pillar[5]arenes, including both homo- and hetero-rimmed ones, with excellent enantioselectivities. Attractively, the resultant planar chiral pillar[5]arenes show great potential for widespread use in many areas such as chiral luminescent materials. This work not only enables the successful synthesis of planar chiral pillar[5]arenes with abundant structural and functional diversity as key building blocks for practical applications but also enriches the asymmetric cross-coupling methodologies in organic synthetic chemistry.

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“…However, fabricating fully organic polymeric CPL materials with tunable handedness and a large dissymmetric factor ( g lum ) remains challenging. The control of the handedness of helical polymers is a promising approach to obtaining organic CPL materials [25–27] …”

Section: Introductionmentioning

confidence: 99%

Visible Helicity Induction and Memory in Polyallene toward Circularly Polarized Luminescence, Helicity Discrimination, and Enantiomer Separation

Gao

et al. 2023

Angew Chem Int Ed

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Inspired by biological helices (e.g., DNA), artificial helical polymers have attracted intense attention. However, precise synthesis of one-handed helices from achiral materials remains a formidable challenge. Herein, a series of achiral poly(biphenyl allene)s with controlled molar mass and low dispersity were prepared and induced into one-handed helices using chiral amines and alcohols. The induced one-handed helix was simultaneously memorized, even after the chiral inducer was removed. The switchable induction processes were visible to naked eye; the achiral polymers exhibited blue emission (irradiated at 365 nm), whereas the induced one-handed helices exhibited cyan emission with clear circularly polarized luminescence. The induced helices formed stable gels in various solvents with helicity discrimination ability: the same-handed helix gels were self-healing, whereas the gels of opposite-handed helicity were self-sorted. Moreover, the induced helices could separate enantiomers via enantioselective crystallization with high efficiency and switchable enantioselectivity.

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AIE‐Active Chiral [3]Rotaxanes with Switchable Circularly Polarized Luminescence

Cited by 30 publications

References 115 publications

Sequence Matters: Precise Synthesis of Hetero[3]rotaxane Isomers with Sequence-dependent Chemical Reactivity and Circularly Polarized Luminescence

Sequence Matters: Precise Synthesis of Hetero[3]rotaxane Isomers with Sequence-dependent Chemical Reactivity and Circularly Polarized Luminescence

Catalytic Enantioselective Synthesis of Planar Chiral Pillar[5]arenes via Asymmetric Sonogashira Coupling

Visible Helicity Induction and Memory in Polyallene toward Circularly Polarized Luminescence, Helicity Discrimination, and Enantiomer Separation

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