Chirality‐Controlled Self‐Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir–Blodgett Thin Films

Holec, Jan; Rybáček, Jiří; Vacek, Jaroslav; Karras, Manfred; Bednářová, Lucie; Budêšínský, Miloś; Slušná, Michaela; Holý, Petr; Schmidt, Bernd; Stará̈, Irena G.; Starý, Ivo

doi:10.1002/chem.201901695

Cited by 11 publications

(12 citation statements)

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“…320 Very recently, Starýand co-workers studied the ECD properties of highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo [6]helicene as Langmuir−Blodgett films, discussing the impact of molecular chirality and chemical nature of the polar group (i.e., ester vs carboxyl vs hydroxyl) on the self-assembly at the air−water interface. 321 Although 1,1′-binaphthyl derivatives (and other similar biaryl compounds with axial chirality) have represented a milestone in the field of solution ECD measurements (especially for conformational analysis), 56 for a long time the chiroptical investigation of their thin films was only little considered; some papers describing second-harmonic generation circular dichroism (SHG-CD) experiments of enantiopure 1,1′-bi-2-naphthol (BINOL) monolayers at the air/quartz surface were published in 1994 by Hicks and co-workers, 279,322,323 while in 2005 a similar SHG-CD study was performed by Conboy et al on Langmuir−Blodgett−Schaefer thin films of (S)-and (R)-BINOL. 324 However, in the last 10 years, the ECD study of 1,1′-binaphthyl derivatives in thin films gained considerable interest.…”

Section: Ecd In Thin Films Of π-Conjugated Small Moleculesmentioning

confidence: 99%

“…In 2018, Iimura et al reported a detailed investigation on the helically distorted [1,1′-bibenzo[ c ]phenanthrene]-2,2′-diol (HEBPOL): thanks to the amphiphilic character arising from the presence of both hydrophobic aromatic rings and hydrophilic −OH groups, it is able to form stable layers at the air–water interface, which were transferred to solid substrates by Langmuir–Blodgett technique; the ECD properties of the obtained films were then investigated and compared with those of spin-coated samples . Very recently, Starý and co-workers studied the ECD properties of highly enantioenriched 3-methoxycarbonyl, 3-carboxy, and 3-hydroxymethyl derivatives of dibenzo[6]helicene as Langmuir–Blodgett films, discussing the impact of molecular chirality and chemical nature of the polar group (i.e., ester vs carboxyl vs hydroxyl) on the self-assembly at the air–water interface …”

Section: Ecd Properties In Thin Films Of π-Conjugated Systems: Litera...mentioning

confidence: 99%

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Chiroptical Properties in Thin Films of π-Conjugated Systems

2020

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Chiral π-conjugated molecules provide new materials with outstanding features for current and perspective applications, especially in the field of optoelectronic devices. In thin films, processes such as charge conduction, light absorption, and emission are governed not only by the structure of the individual molecules but also by their supramolecular structures and intermolecular interactions to a large extent. Electronic circular dichroism, ECD, and its emission counterpart, circularly polarized luminescence, CPL, provide tools for studying aggregated states and the key properties to be sought for designing innovative devices. In this review, we shall present a comprehensive coverage of chiroptical properties measured on thin films of organic π-conjugated molecules. In the first part, we shall discuss some general concepts of ECD, CPL, and other chiroptical spectroscopies, with a focus on their applications to thin film samples. In the following, we will overview the existing literature on chiral π-conjugated systems whose thin films have been characterized by ECD and/or CPL, as well other chiroptical spectroscopies. Special emphasis will be put on systems with large dissymmetry factors (g abs and g lum) and on the application of ECD and CPL to derive structural information on aggregated states.

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Section: Ecd In Thin Films Of π-Conjugated Small Moleculesmentioning

confidence: 99%

Section: Ecd Properties In Thin Films Of π-Conjugated Systems: Litera...mentioning

confidence: 99%

Chiroptical Properties in Thin Films of π-Conjugated Systems

2020

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“…Holec et al researched the behavior of chiral amphiphilic dibenzo [6]helicenes at the air−water interface and their transferred LB films (Figure 19). 147 Although these compounds do not possess long alkyl chains, their 2D assemblies at the air− water interface are somehow formed. Detailed analyses by surface pressure isotherms, UV−vis spectroscopy, electronic circular dichroism, fluorescence spectroscopy, and atomic force microscopy with the aid of a molecular dynamics computational approach revealed the important roles of compound chirality and attached polar functional groups in their 2D assembled structures.…”

Section: ■ For Applicationsmentioning

confidence: 99%

Don’t Forget Langmuir–Blodgett Films 2020: Interfacial Nanoarchitectonics with Molecules, Materials, and Living Objects

2020

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Designing interfacial structures with nanoscale (or molecular) components is one of the important tasks in the nanoarchitectonics concept. In particular, the Langmuir−Blodgett (LB) method can become a promising and powerful strategy in interfacial nanoarchitectonics. From this viewpoint, the status of LB films in 2020 will be discussed in this feature article. After one section on the basics of interfacial nanoarchitectonics with the LB technique, various recent research examples of LB films are introduced according to classifications of (i) growing research, (ii) emerging research, and (iii) future research. In recent LB research, various materials other than traditional lipids and typical amphiphiles can be used as film components of the LB techniques. Two-dimensional materials, supramolecular structures such as metal organic frameworks, and biomaterials such as DNA origami pieces are capable of working as functional components in the LB assemblies. Possible working areas of the LB methods would cover emerging demands, including energy, environmental, and biomedical applications with a wide range of functional materials. In addition, forefront research such as molecular manipulation and cell fate control is conducted in LB-related interfacial science. The LB technique is a traditional and well-develop methodology for molecular films with a ca. 100 year history. However, there is plenty of room at the interfaces, as shown in LB research examples described in this feature article. It is hoped that the continuous development of the science and technology of the LB method make this technique an unforgettable methodology.

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“…Feng et al [11] have utilized hydrophobic interactions to deposit amide-containing helicenes on alkylated quartz via the Langmuir-Blodgett technique. Some other helicenes that are used for the production of Langmuir-Blodgett thin films include 2-amino[6]helicene derivatives [12], thiohelicene bisquinone [13], and dibenzo[6]helicene derivatives [14].…”

Section: Introductionmentioning

confidence: 99%

Bacterial Antifouling Characteristics of Helicene—Graphene Films

Liu

Bae

et al. 2021

Nanomaterials

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Herein, we describe interfacially-assembled [7]helicene films that were deposited on graphene monolayer using the Langmuir-Schaefer deposition by utilizing the interactions of nonplanar (helicene) and planar (graphene) π–π interactions as functional antifouling coatings. Bacterial adhesion of Staphylococcus aureus on helicene—graphene films was noticeably lower than that on bare graphene, up to 96.8% reductions in bacterial adhesion. The promising bacterial antifouling characteristics of helicene films was attributed to the unique molecular geometry of helicene, i.e., nano-helix, which can hinder the nanoscale bacterial docking processes on a surface. We envision that helicene—graphene films may eventually be used as protective coatings against bacterial antifouling on the electronic components of clinical and biomedical devices.

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Chirality‐Controlled Self‐Assembly of Amphiphilic Dibenzo[6]helicenes into Langmuir–Blodgett Thin Films

Cited by 11 publications

References 38 publications

Chiroptical Properties in Thin Films of π-Conjugated Systems

Chiroptical Properties in Thin Films of π-Conjugated Systems

Don’t Forget Langmuir–Blodgett Films 2020: Interfacial Nanoarchitectonics with Molecules, Materials, and Living Objects

Bacterial Antifouling Characteristics of Helicene—Graphene Films

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