Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

Engineering applications of synthetic polymers are widespread due to their availability, processability, low density, and diversity of mechanical properties (Figure 1a). Despite their ubiquitous nature, modern polymers are evolving into multifunctional systems with highly sophisticated behavior. These emergent functions are commonly described as “smart” characteristics whereby “intelligence” is rooted in a specific response elicited from a particular stimulus. Materials that exhibit stimuli-responsive functions thus achieve a desired output (O, the response) upon being subjected to a specific input (I, the stimulus). Given that mechanical loading is inevitable, coupled with the wide range of mechanical properties for synthetic polymers, it is not surprising that mechanoresponsive polymers are an especially attractive class of smart materials. To design materials with stimuli-responsive functions, it is helpful to consider the I-O relationship as an energy transduction process. Achieving the desired I-O linkage thus becomes a problem in finding how to transform energy from the stimulus into energy that executes the desired response. The underlying mechanism that forms this I-O coupling need not be a direct, one-step transduction event; rather, the overall process may proceed through a sequence of energy transduction steps. In this regard, the network of energy transduction pathways is a useful roadmap for designing stimuli-responsive materials (Figure 1b). It is the purpose of this review to broadly survey the mechanical to chemical * To whom correspondence should be addressed. Phone: 217-244-4024. Fax: 217-244-8024. E-mail: jsmoore@illinois.edu. † Department of Chemistry and Beckman Institute. ‡ Department of Materials Science and Engineering and Beckman Institute. § Department of Aerospace Engineering and Beckman Institute. Chem. Rev. XXXX, xxx, 000–000 A

Mechanically-induced chemical changes in polymeric materials

Low band gap (Eg < 1.5 eV) polycyclic hydrocarbons have become one of the most important types of materials for many applications, for example, as semiconductors in organic field effect transistors (OFETs), as light-harvesting dyes in organic solar cells and photodetectors, as near infrared (NIR) fluorescent probes in high resolution bio-imaging and bio-sensing, and as chromophores in non-linear optics. The benzenoid polycyclic hydrocarbons as nano-sized graphene fragments also serve as perfect model compounds to understand the fundamental structure–property relationship of graphene. The ground state of these molecules can be described as either a closed-shell or an open-shell structure on the basis of their molecular size and edge structure. In this review, a summary will be given on a series of low band gap polycyclic hydrocarbons about their synthesis, physical properties and material applications.

Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals

We first fabricated the superhydrophobic film with a water contact angle of 178° based on a perpendicular nanopin fractal structure by a bottom-up process. Until now, only materials with an original water contact angle larger than 90°, which is classified as hydrophobicity, could be used to fabricate the superhydrophobic film (>170°) according to the possible fractal structure by a top-down process. Now, in this work, a water contact angle of about 178° can be achieved using a lauric acid-coated film with an original contact angle of 75°, which is classified as hydrophilicity, based on an ideal fractal structure for the superhydrophobic surface which is fabricated by the nanosize pin with 6.5 nm diameter.

Superhydrophobic Perpendicular Nanopin Film by the Bottom-Up Process

We report the control of molecular orientation in solid films through self-organization and induced-orientation processes. We synthesized water-soluble cationic 3,4,9,10-perylene diimide (1) and studied its self-organization in aqueous solution. By UV−vis spectroscopy, H-aggregates of 1 were observed forming in solutions with concentrations as low as 10-7 M. At concentrations above approximately 0.1 M (7% w/w), these solutions were observed with polarized microscopy to form a chromonic N phase (a nematic lyotropic liquid crystalline phase) at room temperature. Upon induced alignment (by shearing) of the chromonic N phase on a glass substrate and removal of solvent, anisotropic solid films of the dichroic dye were produced. These films have dichroic ratio values that routinely exceed 25 and in some cases 30, making them excellent polarizers over the blue and green region. By use of a combination of polarized UV−vis and FT-IR spectroscopies, the orientation of the average molecular plane in these films was ...

Controlling Molecular Orientation in Solid Films via Self-Organization in the Liquid-Crystalline Phase

/pdf/ionic-quaterrylenebis-dicarboximide-a-novel-mesogen-and-long-449hlhu3vy.pdf

Ionic Quaterrylenebis(dicarboximide): A Novel Mesogen and Long‐Wavelength Polarizing Material

https://www.rsc.org/suppdata/CC/b5/b508220j/b508220j.pdf

Template-guided organization of chromonic liquid crystals into micropatterned anisotropic organic solids.

The synthesis of an ionic quaterrylenebis(dicarboximide) 1a, a long-wavelength absorbing mesogen, is described. When compared with its analogue 2a, an ionic perylenebis(dicarboximide), the aromatic protons of 1a exchange with deuterium of concentrated D(2)SO(4) at a dramatically faster rate. In addition, stronger aggregation in aqueous media was observed for 1a.

Synthesis and Studies of the Properties of a Liquid-Crystalline Quaterrylenebis(dicarboximide) by 1H NMR and UV−vis Spectroscopies

Microfabrication of Anisotropic Organic Materials via Self-Organization of an Ionic Perylenemonoimide

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