Peptide‐Driven Charge‐Transfer Organogels Built from Synergetic Hydrogen Bonding and Pyrene–Naphthalenediimide Donor–Acceptor Interactions

Bartocci, Silvia; Berrocal, José Augusto; Guarracino, Paola; Grillaud, Maxime; Franco, Lorenzo; Míriam,

doi:10.1002/chem.201704487

Cited by 30 publications

(29 citation statements)

References 74 publications

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“…Combination of donor and acceptor chromophore dyes in one molecule results in intramolecular charge transfer, which decreases the HOMO–LUMO band gap and shifts the absorption and emission maxima to higher wavelengths . Bartocci et al reported supramolecular gels from functionalized naphthalene bisimide and pyrene system using donor–acceptor interactions and charge transfer between the two moieties. Solar cell acceptors based on perylene bisimide coupled with pyrene demonstrated promising power conversion efficiency, which was due to the broad absorption and π‐electron delocalization leading to effective charge transport , .…”

Section: Introductionmentioning

confidence: 99%

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

2020

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Polycyclic aromatic hydrocarbon with extended conjugation and broad absorption properties are interesting due to their easy accessibility, response to external stimuli and high stability. Herein, we report synthesis and full characterization of four compounds having multiple photoactive units in conjugation with a central pyrene group. The compound 2 with extended conjugation showed high fluorescence intensity in the solid state. Since the target molecules are non‐toxic and highly fluorescent, water dispersible nanoparticles were prepared from these molecules and explored for cellular imaging.

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Section: Introductionmentioning

confidence: 99%

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

2020

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“…Such a narrow space of 3.47 Å between NDI/pyrene and NDI/NDI leads to strong π⋅⋅⋅π interactions between these aromatic units, thus offering highly effective charge transfer interactions [27, 28] . As a result, we observed the original light‐yellow color of Ca‐NDI crystal become red for Py@Ca‐NDI crystal (Figure S8), indicating the occurrence of charge transfer interaction between NDI and pyrene [29] . Moreover, this highly ordered structure also results in the extensive electron delocalization and communication within such a host–guest MOF skeleton, which is supported by red‐shift absorption [27, 28] .…”

Section: Figurementioning

confidence: 88%

Self‐Assembled Metal–Organic Framework Stabilized Organic Cocrystals for Biological Phototherapy

et al. 2021

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Organic self‐assembled co‐crystals have garnered considerable attention due to their facile synthesis and intriguing properties, but supramolecular interactions restrict their stability in aqueous solution, which is especially important for biological applications. Herein, we report on the first biological application of aqueous dispersible self‐assembled organic co‐crystals via the construction of metal–organic framework (MOF) ‐stabilized co‐crystals. In particular, we built an electron‐deficient MOF with naphthalene diimide (NDI) as the ligand and biocompatible Ca2+ as the metal nodes. An electron donor molecule, pyrene, was encapsulated to form the host–guest MOF self‐assembled co‐crystal. We observed that such MOF structure leads to uniquely high‐density ordered arrangement and the close intermolecular distance (3.47 Å) of the charge transfer pairs. Hence, the concomitant superior charge transfer interaction between pyrene/NDI can be attained and the resultant photothermal conversion efficiency of Py@Ca‐NDI in aqueous solution can thus reach up to 41.8 %, which, to the best of our knowledge, is the highest value among the reported organic co‐crystal materials; it is also much higher than that of the FDA approved photothermal agent ICG as well as most of the reported MOFs. Based on this realization, as a proof of concept, we demonstrated that such a self‐assembled organic co‐crystal platform can be used in biological applications that are exemplified via highly effective long wavelength light photothermal therapy.

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“…Hydrogen bonds, the interactions that occur between hydrogen atoms and a great number of electronegative atoms in biomolecules, play important roles in the formation of biological nanomaterials [49,50,51]. In the process of biomolecular self-assembly, the hydrogen bonds can promote the growth of biomolecules in one direction with a long-range order to form one-dimensional (1D) nanostructures.…”

Section: Internal Interactions Towards Biomolecular Self-assemblymentioning

confidence: 99%

Controlling the Self-Assembly of Biomolecules into Functional Nanomaterials through Internal Interactions and External Stimulations: A Review

et al. 2019

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Biomolecular self-assembly provides a facile way to synthesize functional nanomaterials. Due to the unique structure and functions of biomolecules, the created biological nanomaterials via biomolecular self-assembly have a wide range of applications, from materials science to biomedical engineering, tissue engineering, nanotechnology, and analytical science. In this review, we present recent advances in the synthesis of biological nanomaterials by controlling the biomolecular self-assembly from adjusting internal interactions and external stimulations. The self-assembly mechanisms of biomolecules (DNA, protein, peptide, virus, enzyme, metabolites, lipid, cholesterol, and others) related to various internal interactions, including hydrogen bonds, electrostatic interactions, hydrophobic interactions, π–π stacking, DNA base pairing, and ligand–receptor binding, are discussed by analyzing some recent studies. In addition, some strategies for promoting biomolecular self-assembly via external stimulations, such as adjusting the solution conditions (pH, temperature, ionic strength), adding organics, nanoparticles, or enzymes, and applying external light stimulation to the self-assembly systems, are demonstrated. We hope that this overview will be helpful for readers to understand the self-assembly mechanisms and strategies of biomolecules and to design and develop new biological nanostructures or nanomaterials for desired applications.

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Peptide‐Driven Charge‐Transfer Organogels Built from Synergetic Hydrogen Bonding and Pyrene–Naphthalenediimide Donor–Acceptor Interactions

Cited by 30 publications

References 74 publications

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

Self‐Assembled Metal–Organic Framework Stabilized Organic Cocrystals for Biological Phototherapy

Controlling the Self-Assembly of Biomolecules into Functional Nanomaterials through Internal Interactions and External Stimulations: A Review

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