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

Ozcelik, Ani; Pereira-Cameselle, Raquel; Weber, Alexander von; Paszkiewicz, Mateusz; Carlotti, Marco; Paintner, Tobias; Zhang, L.; Lin, Tao; Zhang, Y.-Q.; Barth, Johannes V.; Nobelen, T. van den; Chiechi, Ryan C.; Jakob, Matthias; Heiz, Ulrich; Chiussi, S.; Kartouzian, Aras; Klappenberger, Florian; Alonso‐Gómez, José Lorenzo

doi:10.1021/acs.langmuir.8b00305

Cited by 23 publications

(39 citation statements)

References 61 publications

(105 reference statements)

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“…The anisotropy factor is also called g value and allows for the comparison of optical activity among various samples. We used the method of second harmonic generation circular dichroism (SHG‐CD) to evaluate the chiroptical response of upstanding chiral architectures, which are a group of surface bond allenes, possessing high stability and optical activity . We could demonstrate the superiority of SHG‐CD to CD measurements by recording the circular dichroism in a single monolayer of adsorbed molecules at a single wavelength .…”

Section: Spectroscopic Methods To Analyze Model Heterogeneous Asymmetmentioning

confidence: 99%

“…We used the method of second harmonic generation circular dichroism (SHG‐CD) to evaluate the chiroptical response of upstanding chiral architectures, which are a group of surface bond allenes, possessing high stability and optical activity . We could demonstrate the superiority of SHG‐CD to CD measurements by recording the circular dichroism in a single monolayer of adsorbed molecules at a single wavelength . More recently, we applied SHG‐CD to record nonlinear spectra for the anisotropy factor of 1,1′‐bi‐2‐naphthol on glass and demonstrated the submonolayer sensitivity of the technique .…”

Section: Spectroscopic Methods To Analyze Model Heterogeneous Asymmetmentioning

confidence: 99%

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Spectroscopy for model heterogeneous asymmetric catalysis

Kartouzian¹

2019

Chirality

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Heterogeneous catalysis has vastly benefited from investigations performed on model systems under well‐controlled conditions. The application of most of the techniques utilized for such studies is not feasible for asymmetric reactions as enantiomers possess identical physical and chemical properties unless while interacting with polarized light and other chiral entities. A thorough investigation of a heterogeneous asymmetric catalytic process should include probing the catalyst prior to, during, and after the reaction as well as the analysis of reaction products to evaluate the achieved enantiomeric excess. I present recent studies that demonstrate the strength of chiroptical spectroscopic methods to tackle the challenges in investigating model heterogeneous asymmetric catalysis covering all the abovementioned aspects.

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Section: Spectroscopic Methods To Analyze Model Heterogeneous Asymmetmentioning

confidence: 99%

Section: Spectroscopic Methods To Analyze Model Heterogeneous Asymmetmentioning

confidence: 99%

Spectroscopy for model heterogeneous asymmetric catalysis

Kartouzian¹

2019

Chirality

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“…Whereas chiroptical solutions are by far the most abundant, little is known regarding the construction of two‐dimensional (2D) chiroptical surfaces that could be employed in daily life. Among other strategies, the inherent chirality of small organic molecules could be bestowed upon metal surfaces by self‐assembly . To this end, we employed chiral framework (CF) CF‐1 bearing allenes on Ag (111) under vacuum conditions (Figure A).…”

Section: Introductionmentioning

confidence: 99%

“…To tackle this challenge, we undertook the strategy of self‐assembled monolayers (SAMs) and synthesized both enantiomers of thioacetate‐derivatized CF‐2 for the functionalization of Au surfaces (Figure B). Remarkably, the chiroptical responses of the formed nanoarchitectures were addressed by means of second harmonic generation CD spectroscopy on a custom‐made transparent substrate . However, allenes may undergo photoisomerization, limiting their exploitation for everyday applications.…”

Section: Introductionmentioning

confidence: 99%

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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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Enantiospecific Desorption Triggered by Circularly Polarized Light

et al. 2019

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The interest in enantioseparation and enantiopurification of chiral molecules has been drastically increasing over the past decades,since these are important steps in various disciplines such as pharmaceutical industry,asymmetric catalysis,a nd chiral sensing.B ye xposing racemic samples of BINOL (1,1'-bi-2-naphthol) coated onto achiral glass substrates to circularly polarized light, we unambiguously demonstrate that by controlling the handedness of circularly polarized light, preferential desorption of enantiomers can be achieved. There are currently no mechanisms knownt hat would describe this phenomenon. Our observation together with as implified phenomenological model suggests that the process of laser desorption needs to be further developed and the contribution of quantum mechanical processes should be revisited to account for these data. Asymmetric laser desorption provides us with ac ontamination-free technique for the enantioenrichment of chiral compounds.

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

Cited by 23 publications

References 61 publications

Spectroscopy for model heterogeneous asymmetric catalysis

Spectroscopy for model heterogeneous asymmetric catalysis

Design and synthesis of chiral spirobifluorenes

Enantiospecific Desorption Triggered by Circularly Polarized Light

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