Modulating Noncovalent Cross-links with Molecular Switches

Epstein, Eric S.; Martinetti, Luca; Kollarigowda, Ravichandran H.; Torre, Olivia Carey-De La; Moore, Jeffrey S.; Ewoldt, Randy H.

doi:10.1021/jacs.8b12762

Cited by 31 publications

(34 citation statements)

References 60 publications

(84 reference statements)

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“…In this respect, there has been much progress in the creation of artificial DNA prototypes to program molecular functions, 2,3 adapting both supramolecular 4−8 and dynamic covalent interactions. 9−12 Despite these successes in pursuit of artificial life, the advent of synthetic chemistry in this field remains far slower than their biochemistry counterparts. 13−16…”

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confidence: 99%

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

et al. 2019

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The development of a synthetic code that enables a sequence programmable feature like DNA represents a key aspect toward intelligent molecular systems. We developed herein the well-known dynamic covalent interaction between boronic acids (BAs) and catechols (CAs) into synthetic nucleobase analogs. Along a defined peptide backbone, BA or CA residues are arranged to enable sequence recognition to their complementary strand. Dynamic strand displacement and errors were elucidated thermodynamically to show that sequences are able to specifically select their partners. Unlike DNA, the pH dependency of BA/CA binding enables the dehybridization of complementary strands at pH 5.0. In addition, we demonstrate the sequence recognition at the macromolecular level by conjugating the cytochrome c protein to a complementary polyethylene glycol chain in a site-directed fashion.

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confidence: 99%

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

et al. 2019

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“…There is no very clear trend found on the relationship between the substituents (electron‐donating or electron‐withdrawing group) of aldehydes and the yield of the target spiropyrans. At last, our strategy was tested on the synthesis of SP–C1 and SP–C2 with iodomethane and 2‐bromoethanol as the alkylating reagents, which provided the desired products in competitive or even higher yields than reported ones . (entry 10 & 11) If taking the overall cost on chemicals, time on the reactions and workups into account, the advantage of the new developed one‐pot synthesis of spiropyrans is attractive to the researchers.…”

Section: Figurementioning

confidence: 99%

One‐Pot Synthesis of Spiropyrans

et al. 2019

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A highly efficient one-pot synthetic strategy for the preparation of spiropyrans was developed. The method is free of special equipment and operations, and meanwhile, it is energy-and time-saving compared to the reported three-step procedures. Tolerated with various solvents, bases, aldehydes, and alkyl bromides, the commonly used "T-type" spiropyrans (SP1 s) were synthesized in one-pot with highly improved yields. To avoid the hydrolysis of the spiropyran moiety during the synthesis of the linear type spiropyrans (SP2 s), a strategy of the combination of pre-alkylation of phenolic hydroxyl group of 5-hydroxy-indole and a one-pot synthesis of the spiropyran moiety was also designed. With a short reaction time, simplified workups, and reduced chemical waste, this onepot synthetic strategy for the synthesis of spiropyran compounds would facilitate related research in the fields of biology and materials science, and would be attractive to the industrial application.[a] Dr.

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“…The relaxation process is usually too lengthy (taking several minutes to hours) to be considered for real applications. The use of noncovalent bonds presents an attractive strategy to construct polymeric materials with a number of unique properties such as shape memory, [ 34 ] stimulus‐responsiveness, [ 35–38 ] good processability, [ 39,40 ] toughness, [ 41 ] and self‐healing. [ 42,43 ] However, due to its highly dynamic nature and relatively weak strength, the extruded filaments could easily undergo fast dynamic exchange, leading to short‐term stability as well as relatively poor mechanical properties of printed objects.…”

Section: Introductionmentioning

confidence: 99%

Extrusion 3D Printing of Polymeric Materials with Advanced Properties

et al. 2020

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3D printing is a rapidly growing technology that has an enormous potential to impact a wide range of industries such as engineering, art, education, medicine, and aerospace. The flexibility in design provided by this technique offers many opportunities for manufacturing sophisticated 3D devices. The most widely utilized method is an extrusion‐based solid‐freeform fabrication approach, which is an extremely attractive additive manufacturing technology in both academic and industrial research communities. This method is versatile, with the ability to print a range of dimensions, multimaterial, and multifunctional 3D structures. It is also a very affordable technique in prototyping. However, the lack of variety in printable polymers with advanced material properties becomes the main bottleneck in further development of this technology. Herein, a comprehensive review is provided, focusing on material design strategies to achieve or enhance the 3D printability of a range of polymers including thermoplastics, thermosets, hydrogels, and other polymers by extrusion techniques. Moreover, diverse advanced properties exhibited by such printed polymers, such as mechanical strength, conductance, self‐healing, as well as other integrated properties are highlighted. Lastly, the stimuli responsiveness of the 3D printed polymeric materials including shape morphing, degradability, and color changing is also discussed.

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Modulating Noncovalent Cross-links with Molecular Switches

Cited by 31 publications

References 60 publications

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

One‐Pot Synthesis of Spiropyrans

Extrusion 3D Printing of Polymeric Materials with Advanced Properties

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