In the specific context of condensed media, the significant and increasing recent interest in the α-cyanostilbene (CS) motif [ArCHC(CN)Ar] is relevant. These compounds have shown remarkable optical features in addition to interesting electrical properties, and hence they are recognized as very suitable and versatile options for the development of functional materials. This progress report is focused on current and future use of CS structures and molecular assemblies with the aim of exploring and developing for the next generations of functional materials. A critical selection of illustrative materials that contain the CS motif, including relevant subfamilies such as the dicyanodistyrylbenzene and 2,3,3-triphenylacrylonitrile shows how, driven by the self-assembly of CS blocks, a variety of properties, effects, and possibilities for practical applications can be offered to the scientific community, through different rational routes for the elaboration of advanced materials. A survey is provided on the research efforts directed toward promoting the self-assembly of the solid state (polycrystalline solids, thin films, and single crystals), liquid crystals, nanostructures, and gels with multistimuli responsiveness, and applications for sensors, organic light-emitting diodes, organic field effect transistors, organic lasers, solar cells, or bioimaging purposes.
Two-dimensional
(2D) covalent organic frameworks (COFs) are an
emerging class of promising 2D materials with high crystallinity and
tunable structures. However, the low electrical conductivity impedes
their applications in electronics and optoelectronics. Integrating
large π-conjugated building blocks into 2D lattices to enhance
efficient π-stacking and chemical doping is an effective way
to improve the conductivity of 2D COFs. Herein, two nonplanar 2D COFs
with kagome (DHP-COF) and rhombus (c-HBC-COF) lattices
have been designed and synthesized from distorted aromatics with different
π-conjugated structures (flexible and rigid structure, respectively).
DHP-COF shows a highly distorted 2D lattice that hampers stacking,
consequently limiting its charge carrier transport properties. Conversely, c-HBC-COF, with distorted although concave–convex
self-complementary nodes, shows a less distorted 2D lattice that does
not interfere with interlayer π-stacking. Employing time- and
frequency-resolved terahertz spectroscopy, we unveil a high charge-carrier
mobility up to 44 cm2 V–1 s–1, among the highest reported for 2D COFs.
A high degree of crystallinity is an essential aspect in two-dimensional covalent organic frameworks, as many properties depend strongly on the structural arrangement of the different layers and their constituents. We introduce herein a new design strategy based on core-twisted polycyclic aromatic hydrocarbon as rigid nodes that give rise to a two-dimensional covalent organic framework with a wavy honeycomb (chair-like) lattice. The concave-convex self-complementarity of the wavy two-dimensional lattice guides the stacking of framework layers into a highly stable and ordered covalent organic framework that allows a full 3D analysis by transmission electron microscopy revealing its chair-like honeycomb facets and aligned mesoporous channels. Remarkably, the waviness of the framework does not disrupt the interlayer π-π stacking that shows charge transporting properties similar to those of planar covalent organic frameworks. The implementation of core-twisted aromatics as building blocks for covalent organic frameworks brings new possibilities in the design of highly ordered organic materials.
Three-dimensional covalent organic frameworks (3D COFs) with a pcu topology have been obtained from distorted polycyclic aromatic hydrocarbons acting as triangular antiprismatic (D 3d ) nodes. Such 3D COFs are six-fold interpenetrated as the result of interframework p-stacking, which enable charge transport properties that are not expected for 3D COFs.
The in situ on-surface conversion process from boroxine-linked covalent organic frameworks (COFs) to boronate ester-linked COFs is triggered and catalyzed at room temperature by an electric field and monitored with scanning tunneling microscopy (STM). The adaptive behavior within the generated dynamic covalent libraries (DCLs) was revealed, providing in-depth understanding of the dynamic network switching process.
• 2D COFs are porous. Piling-up holey 2D polymers in a periodic fashion gives rise to porous channels, whose structure will depend on both the lattice and the packing. The ability to design and synthesize monomers can affect fundamental aspects in 2D covalent organic frameworks, such as dimensionality, topology, and pore size. Besides this, the structure of the monomers can also affect interlayer interactions, which provide an additional means to influence crystallinity, layer arrangement, interlayer distances, and exfoliability. Herein, some of the effects that the structure of monomers can have on the interlayer interactions in 2D covalent organic frameworks and related materials are illustrated.
Two isomeric cyanostilbene photoswitchable bent‐core mesogens with polar liquid crystal phases in which macroscopic polarization and luminescence can be light‐modulated are introduced. Z/E isomerization or [2+2] cycloaddition photochemical processes occur depending on the chemical structure, which make the compounds very innovative multifunctional advanced materials.
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