A Covalent Organic Helical Cage with Remarkable Chiroptical Amplification

Míguez-Lago, Sandra; Llamas-Saíz, Antonio L.; Cid, Marı́a Magdalena; Alonso‐Gómez, José Lorenzo

doi:10.1002/chem.201503994

Cited by 26 publications

(39 citation statements)

References 46 publications

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“…In this regard, we have used enantiopure diethynylallenes for the synthesis of cyclic and helical oligomers with outstanding chiroptical responses. As a step further towards chiroptical devices, we have incorporated functional groups leading to the recognition of halogenated compounds with pyridoallenophanes, and to the chiroptical detection of sandwich organometallic compounds with covalent organic molecular cages . Additionally, with the aim of expanding the applicability of chiroptical responses, we succeeded in surface functionalization with chiral allenes as up‐standing chiral architectures .…”

Section: Methodsmentioning

confidence: 99%

Diverse Chiral Scaffolds from Diethynylspiranes: All‐Carbon Double Helices and Flexible Shape‐Persistent Macrocycles

Castro‐Fernández

Ren

García

et al. 2017

Chemistry A European J

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State-of-the-art chiroptical spectroscopies are valuable tools for structural elucidation. However, the potential of these spectroscopies for everyday applications has not been exploited to date partially due to the lack of sufficiently stable and efficient chiroptical systems. To this end, the development of suitable chiroptical structures is essential. Herein, we present the synthesis of spiro-compounds (P )-1 and (P )-2 as well as (M )-1 and (M )-2 exhibiting remarkable chiroptical responses. Theoretical simulations show that (P )-1, constituted by two (P)-configured spiranic chiral axes, presents an all-carbon double helix structure with (M)-helicity. On the other hand, molecular dynamic simulations reveal (P )-2 to have a single path for geometry-modification along its flat conformational space, certifying it as a chiral flexible shape-persistent macrocycle. Geometric quantification of chirality has been used to compare the spiranic derivatives presented herein.

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Section: Methodsmentioning

confidence: 99%

Diverse Chiral Scaffolds from Diethynylspiranes: All‐Carbon Double Helices and Flexible Shape‐Persistent Macrocycles

Castro‐Fernández

Ren

García

et al. 2017

Chemistry A European J

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“…Great effort has been accordingly devoted to the development of systems involving purely organic molecules, complexes, or plasmonic nanostructures with remarkable chiroptical properties in solution. In this regard, we have achieved oligomeric, cyclic, or cage‐shaped molecular geometries through axially chiral allenes. From the application point of view, the efficient integration of chiroptical systems into devices is fundamental and hence the state of matter must be carefully chosen to meet the requirements of a specific application.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of chiral spirobifluorenes

2020

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Chiroptical spectroscopic methods serve as a practical tool for the structural characterization of chiral systems based on the interaction with polarized light. The higher sensitivity of these methods, compared with their achiral counterparts, not only enables the determination of absolute configuration and conformational preferences, but also supramolecular interactions may be monitored. In order to expand the applicability of chiroptical systems, the development of functional materials exhibiting intense chiroptical responses is essential. As a proof of principle, we previously constructed chiroptical interfaces via thioacetate‐derivatized allenes. Because of the photoisomerization issues associated with allenes, we have recently proposed their replacement by spirobifluorenes to achieve robust chiroptical systems. Thus, we hereby present the design and synthesis of chiral spirobifluorenes bearing thioacetates suitable for suface functionalization.

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“…1,10 In this regard, there are several studies focused on the design and synthesis of systems presenting enhanced chiroptical responses in the search for applications in solution. [11][12][13][14][15] On the other hand, constructions of chiroptical surfaces is required in order to develop lab-on-a-chip devices. However, the limited knowledge regarding the interfacial integration of chiroptical compounds has hampered to date the emergence of chiroptical sensors for everyday use.…”

Section: Introductionmentioning

confidence: 99%

Device-Compatible Chiroptical Surfaces through Self-Assembly of Enantiopure Allenes

Ozcelik¹,

Pereira-Cameselle²,

Weber

et al. 2018

Langmuir

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Chiroptical methods have been proven to be superior compared to their achiral counterparts for the structural elucidation of many compounds. In order to expand the use of chiroptical systems to everyday applications, the development of functional materials exhibiting intense chiroptical responses is essential. Particularly, tailored and robust interfaces compatible with standard device operation conditions are required. Herein, we present the design and synthesis of chiral allenes and their use for the functionalization of gold surfaces. The self-assembly results in a monolayer-thin room-temperature-stable upstanding chiral architecture as ascertained by ellipsometry, X-ray photoelectron spectroscopy, and near-edge X-ray absorption-fine-structure. Moreover, these nanostructures anchored to device-compatible substrates features intense chiroptical second harmonic generation. Both straight-forward preparation of the device-compatible interfaces along with their chiroptical nature provide major prospects for everyday applications.

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A Covalent Organic Helical Cage with Remarkable Chiroptical Amplification

Cited by 26 publications

References 46 publications

Diverse Chiral Scaffolds from Diethynylspiranes: All‐Carbon Double Helices and Flexible Shape‐Persistent Macrocycles

Diverse Chiral Scaffolds from Diethynylspiranes: All‐Carbon Double Helices and Flexible Shape‐Persistent Macrocycles

Design and synthesis of chiral spirobifluorenes

Device-Compatible Chiroptical Surfaces through Self-Assembly of Enantiopure Allenes

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