Spontaneous self-assembly of designed cyclic dipeptide (Phg-Phg) into two-dimensional nano- and mesosheets

Govindaraju, T.; Makam, Pandeeswar; Jayaramulu, Kolleboyina; Jaipuria, Garima; Atreya, Hanudatta S.

doi:10.1080/10610278.2010.550685

Cited by 48 publications

(42 citation statements)

References 41 publications

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“…Govindaraju's group has extensively investigated their assembly, highlighting interesting properties of these systems, including the increased stability towards proteolysis. [37][38][39] Both supramolecular organogels [40] and hydrogels [41] have been reported based on these structures. Gazit and Reches demonstrated the spontaneous formation and self-assembly of surface-bound arrays of cyclic diphenylalanine peptide nanotubes using chemical vapor deposition.…”

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Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

et al. 2020

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Dipeptides are known to spontaneously cyclize to diketopiperazines, and in some cases these cyclic dipeptides have been shown to self‐assemble to form supramolecular nanostructures. Herein, we demonstrate the in situ cyclization of dipeptide methyl esters in aqueous buffer by intramolecular aminolysis, leading to the formation of diverse supramolecular nanostructures. The chemical nature of the amino acid side chains dictates the supramolecular arrangement and resulting nanoscale architectures. For c[LF], supramolecular gels are formed, and the concentration of starting materials influences the mechanical properties of these hydrogels. Moreover, by adding metalloporphyrins to the starting dipeptide starting solution, these become incorporated through cooperative assembly, resulting in the formation of nanofibers able to catalyse the oxidation of organic phenol in water. The approach taken here, which combines chemically activated assembly with the versatility of short peptides, demonstrates a new and easy method to achieving spontaneous formation of a variety of functional supramolecular materials using simple building blocks.

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Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

et al. 2020

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“…The L ‐ NDI chromophores undergo 1D π – π stacking in a direction perpendicular to the nanosheet surface. However the phenyl ring of phenylalanine facilitates a lateral organization to form 2D nanosheet architectures through interdigitation 24…”

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confidence: 99%

Engineering Molecular Organization of Naphthalenediimides: Large Nanosheets with Metallic Conductivity and Attoliter Containers

Avinash

Govindaraju

2011

Adv Funct Materials

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Molecular‐interaction‐induced organizations are the basis of various biological and nonbiological systems. The molecular recognition process involved in the formation of such systems is rather complicated, as it constitutes a subtle balance of various noncovalent interactions. The molecular organization of electron‐deficient aromatic systems is particularly appealing, as they are the potential candidates for a variety of applications. The main challenge in organizing aromatic moieties lies in controlling and optimizing the relatively strong π–π interactions by appropriate functionalization. Herein, we describe a simple molecular design involving phenylalanine methylester‐functionalized naphthalenediimide (L‐NDI and D‐NDI) to achieve high‐level molecular ordering by solution processing. NDIs are among the most promising organic n‐type semiconductors. However the molecular ordering of these organic entities determines their optimal functioning in an organic device. Highly crystalline free‐floating nanosheets with large lateral dimensions were obtained for the first time through molecularly engineered self‐assembly of L‐NDI and D‐NDI systems. Interestingly the nanosheets exhibit a remarkable conductivity of 1.6 S cm−1. Furthermore the molecular organization of L‐NDI was tuned into container‐like complex architectures by employing chlorinated‐ co‐solvent‐mediated halogen bonding. The composition and the type of chlorinated co‐solvent resulted in the formation of nanocups, mesocups, and bowl‐like architectures. The nanocups possess a net volume of 0.1–1.5 attoliters (10−18 L) and can be used as containers for miniaturized applications.

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“…For this, we employ the simplest forms of peptide, viz. CDPs, which can be tailored into hydrogen bonded one-dimensional (1D) molecular chains or two-dimensional (2D) molecular layers depending on the nature of the side chains 10 11 12 13 14 15 16 . Such materials offer the following important advantages: (i) rigid structural and self-complementary (multiple hydrogen bonding) motifs, (ii) functional tailorability through the introduction of α-substituents to impart additional functionalities or noncovalent interactions, (iii) configurational variability, (iv) biocompatibility, (v) solution processability that entails easy synthesis and scalability.…”

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Bioinspired Reductionistic Peptide Engineering for Exceptional Mechanical Properties

Avinash

Raut

Mishra

et al. 2015

Sci Rep

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A simple solution-processing and self-assembly approach that exploits the synergistic interactions between multiple hydrogen bonded networks and aromatic interactions was utilized to synthesize molecular crystals of cyclic dipeptides (CDPs), whose molecular weights (~0.2 kDa) are nearly three orders of magnitude smaller than that of natural structural proteins (50–300 kDa). Mechanical properties of these materials, measured using the nanoindentation technique, indicate that the stiffness and strength are comparable and sometimes better than those of natural fibres. The measured mechanical responses were rationalized by recourse to the crystallographic structural analysis and intermolecular interactions in the self-assembled single crystals. With this work we highlight the significance of developing small molecule based bioinspired design strategies to emulate biomechanical properties. A particular advantage of the successfully demonstrated reductionistic strategy of the present work is its amenability for realistic industrial scale manufacturing of designer biomaterials with desired mechanical properties.

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Spontaneous self-assembly of designed cyclic dipeptide (Phg-Phg) into two-dimensional nano- and mesosheets

Cited by 48 publications

References 41 publications

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

Engineering Molecular Organization of Naphthalenediimides: Large Nanosheets with Metallic Conductivity and Attoliter Containers

Bioinspired Reductionistic Peptide Engineering for Exceptional Mechanical Properties

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