Synthesis of crystals of Tröger's base analogues and their fluorescence properties

Zhuge, Xiangxue; Liu, Ruichao; Li, Jinyan; Zhang, Jian; Li, Yexin; Yuan, Chunxue

doi:10.1016/j.dyepig.2019.107678

Cited by 8 publications

(5 citation statements)

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“…According to reports, the fluorescence characteristics exhibited by Tröger’s base moieties in the solid state mostly depend on the intensity of the π–π interaction inside the aggregated structures. The fluorescence of Tröger’s base moieties diminished as a result of the increased π–π interaction . Furthermore, it has been observed that the possible subfluorophores, namely, amino and phenol, were effectively immobilized by the cross-linked polymer cluster, resulting in enhanced fluorescence characteristics .…”

Section: Resultsmentioning

confidence: 99%

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Multistep Continuous Synthesis of a Highly Fluorescent Tröger’s Base-Derived Benzoxazine: Its Thermal Conversion into Intrinsic Microporosity Polymers

Ahmed,

EL-Mahdy

2024

Macromolecules

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Troger's base (TB), with its rigid V-shaped geometry, is frequently used as a building block to create polymers with intrinsic microporosity (PIMs). On the other hand, polybenzoxazines have received a lot of attention for a wide range of applications such as high thermal stability, metal ion detection, and cathodic material in batteries. Therefore, in the present work, we describe the first example of Troger's base-derived benzoxazine and its thermal transformation into Troger's base-benzoxazine-derived polymer of intrinsic microporosity. The desired Troger's base-derived benzoxazine is synthesized through a continuous three-step (Schiff base, reduction, and Mannich) approach starting from Troger's base, 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f ][1,5]diazocine-3,9-diamine, with no intermediate isolation and purification, and its transformation into Troger's base-benzoxazine-derived PIM is performed through ring-opening polymerization. The continuous threestep synthesis approach for Troger's base-derived benzoxazine and the formation of Troger's base-benzoxazine-derived PIM has never been reported previously. The chemical structure of Troger's base-derived benzoxazine is established using Fourier transform infrared (FTIR), nuclear magnetic resonance spectroscopy, and DFT calculations. The thermal formation and curing behavior of Troger's base-benzoxazine-derived PIM are monitored using FTIR, differential scanning calorimetry, and thermogravimetric analysis. Interestingly, the fluorescence emission of Troger's base-benzoxazine is observed to be significantly pronounced exclusively in a solution state. Conversely, Troger's base-benzoxazine-derived PIM exhibits a notable fluorescence emission solely in the solid state. Furthermore, the emission maximum of the PIM undergoes a red shift when the curing temperature is increased. The present research is expected to result in the development of a thermally stable benzoxazine-derived PIM that can be cured, and its degree of curing can be measured by monitoring the change in the fluorescence color.

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Section: Resultsmentioning

confidence: 99%

“…The fluorescence of Troger's base moieties diminished as a result of the increased π−π interaction. 103 Furthermore, it has been observed that the possible subfluorophores, namely, amino and phenol, were effectively immobilized by the cross-linked polymer cluster, resulting in enhanced fluorescence characteristics. 104…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Multistep Continuous Synthesis of a Highly Fluorescent Tröger’s Base-Derived Benzoxazine: Its Thermal Conversion into Intrinsic Microporosity Polymers

Ahmed,

EL-Mahdy

2024

Macromolecules

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“…2 and 5). This interlocked assembly is tight to an extreme extent that enables the rigid aromatic wings of TBA to impose their orientation 11,13 onto the enclosed part of CBPQTÁ4PF 6 and twists (Fig. 5) its confined pyridinium residues in order to fit and host them in the L-shape chiral cavity of the Tro ¨gerophane.…”

Section: Resultsmentioning

confidence: 99%

A nitrogen-based chiral catenane for enantioenriching photocatalytic aerobic oxidation

Kazem‐Rostami

2022

New J. Chem.

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“…TBAs are a class of exceptionally chiral diamines whose structural rigidity prevents nitrogen inversion. TBAs have been employed in the design of phosphorescent organic light-emitting diodes (OLEDs) [30,31], molecular switches [32], supramolecular scaffolding [33], liquid crystal dopants [34], artificial muscles [35], metalloporphyrins [36], photosensitizers [37], fluorosolvatochromic, fluorescent and NMR active probes [38][39][40][41][42], macrocycles [43,44], perovskite solar cells [45], chiral catenanes [46], ultra-microporous, and gas separating membranes [47][48][49].…”

Section: Introductionmentioning

confidence: 99%

Enantiopurification by Co-Crystallization within Cyclodextrin Metal–Organic Framework

Kazem-Rostami,

Shirdast,

Mainali

2024

Crystals

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Tröger’s base analogs (TBAs) and their derivatives are versatile, Λ-shaped, tetracyclic chiral building blocks utilized in numerous fields of research. Although various methods for the enantiopurification of TBAs have been demonstrated in the literature, none has achieved it with the use of metal–organic frameworks (MOFs). This investigation introduces a convenient and scalable method to obtain enantiopure TBAs with the formation and digestion of a chiral MOF composed of fully recoverable and non-hazardous starting materials, namely, cyclodextrin-based metal–organic framework (CD-MOF).

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Synthesis of crystals of Tröger's base analogues and their fluorescence properties

Cited by 8 publications

References 50 publications

Multistep Continuous Synthesis of a Highly Fluorescent Tröger’s Base-Derived Benzoxazine: Its Thermal Conversion into Intrinsic Microporosity Polymers

Multistep Continuous Synthesis of a Highly Fluorescent Tröger’s Base-Derived Benzoxazine: Its Thermal Conversion into Intrinsic Microporosity Polymers

A nitrogen-based chiral catenane for enantioenriching photocatalytic aerobic oxidation

Enantiopurification by Co-Crystallization within Cyclodextrin Metal–Organic Framework

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