Innentitelbild: Amphiphilic Self‐Assembly of an n‐Type Nanotube (Angew. Chem. 42/2010)

Shao, Hui; Seifert, James; Romano, Natalie C.; Gao, Min; Helmus, Jonathan; Jaroniec, Christopher P.; Modarelli, David A.; Parquette, Jon R.

doi:10.1002/ange.201005441

Cited by 4 publications

(1 citation statement)

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“…NDIs can be used in several biomedical applications due to their sensing, DNA intercalation, antimicrobial, and anticarcinogenic properties 4, 5. In addition to its remarkable molecular characteristics, the morphology of the derived nanomaterials has a profound influence on their optimal functioning 6–11. In this article we describe a novel supramolecularly engineered organization of NDIs into nanosheets, nanocups, mesocups, and bowl‐like complex architectures.…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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Hydrogen‐Bonding‐Mediated J‐Aggregation and White‐Light Emission from a Remarkably Simple, Single‐Component, Naphthalenediimide Chromophore

Molla

Ghosh

2012

Chemistry A European J

124

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Hydrogen‐Bonding‐Mediated Vesicular Assembly of Functionalized Naphthalene–Diimide‐Based Bolaamphiphile and Guest‐Induced Gelation in Water

Molla

Ghosh

2012

Chemistry A European J

115

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This paper describes the spontaneous vesicular assembly of a naphthalene-diimide (NDI)-based non-ionic bolaamphiphile in aqueous medium by using the synergistic effects of π-stacking and hydrogen bonding. Site isolation of the hydrogen-bonding functionality (hydrazide), a strategy that has been adopted so elegantly in nature, has been executed in this system to protect these moieties from the bulk water so that the distinct role of hydrogen bonding in the self-assembly of hydrazide-functionalized NDI building blocks could be realized, even in aqueous solution. Furthermore, the electron-deficient NDI-based bolaamphiphile could engage in donor-acceptor (D-A) charge-transfer (CT) interactions with a water-insoluble electron-rich pyrene donor by virtue of intercalation of the latter chromophore in between two NDI building blocks. Remarkably, even when pyrene was located between two NDI blocks, intermolecular hydrogen-bonding networks between the NDI-linked hydrazide groups could be retained. However, time-dependent AFM studies revealed that the radius of curvature of the alternately stacked D-A assembly increased significantly, thereby leading to intervesicular fusion, which eventually resulted in rupturing of the membrane to form 1D fibers. Such 2D-to-1D morphological transition produced CT-mediated hydrogels at relatively higher concentrations. Instead of pyrene, when a water-soluble carboxylate-functionalized pyrene derivative was used as the intercalator, non-covalent tunable in-situ surface-functionalization could be achieved, as evidenced by the zeta-potential measurements.

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Innentitelbild: Amphiphilic Self‐Assembly of an n‐Type Nanotube (Angew. Chem. 42/2010)

Cited by 4 publications

References 0 publications

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

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

Hydrogen‐Bonding‐Mediated J‐Aggregation and White‐Light Emission from a Remarkably Simple, Single‐Component, Naphthalenediimide Chromophore

Hydrogen‐Bonding‐Mediated Vesicular Assembly of Functionalized Naphthalene–Diimide‐Based Bolaamphiphile and Guest‐Induced Gelation in Water

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