Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

Avinash, M. B.; Sandeepa, K V; Govindaraju, T.

doi:10.3762/bjoc.9.178

Cited by 9 publications

(6 citation statements)

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“…ADA, triads (88) . They found that a relatively weak noncovalent CT interaction was achieved using symmetric and p-complementary pyrene and NDI . The Pantoş group studied, for the first time, the strength of aromatic donor–acceptor interactions between NDI and DAN derivatives within polymers using nonpolar solvents …”

Section: Supramolecular Self-assemblymentioning

confidence: 99%

“…They found that a relatively weak noncovalent CT interaction was achieved using symmetric and p-complementary pyrene and NDI. 212 The Pantoşgroup studied, for the first time, the strength of aromatic donor−acceptor interactions between NDI and DAN derivatives within polymers using nonpolar solvents. 213 Sanders et al 214 report the synthesis, self-assembly, and electron-transfer capabilities of peptide-based electron acceptor−donor−acceptor (A-D-A) systems.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). It explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion-π interactions; and NDI intercalations with DNA for medicinal applications. We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. Also presented are some interesting synthetic routes and procedures that can be used toward further development of NDI-bearing compounds for future applications. Finally, we conclude with our views on NDI chemistry for future research endeavors, and we outline what we believe are the key obstacles that need to be overcome for NDIs to see real world applications.

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Section: Supramolecular Self-assemblymentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

et al. 2016

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“…NDI is a highly π-acidic planar molecule with an estimated molecular quadrupole moment ( Q zz ) of +18.6 B (Buckinghams) that forms a unique pair with π-basic pyrene ( Q zz = −13.8 B) due to their topological structural similarity and the complementary π-character. ,, The alternate stacks of electron donor–acceptor based CT complexation is especially interesting due to high electrical conductivity and room-temperature ferroelectricity. − However, the interaction energy for NDI–NDI (−27.17 kcal mol –1 ) stack is greater than those for NDI–pyrene (−23.35 kcal mol –1 ) and pyrene–pyrene (−16.45 kcal mol –1 ), and thereby self-sorting predominates over alternate stacking . We showed that NDI–pyrene dyads prefer alternate stacking (−53.62 kcal mol –1 ) over self-sorted assemblies (−43.62 kcal mol –1 ).…”

Section: Molecular Architectonicsmentioning

confidence: 99%

Architectonics: Design of Molecular Architecture for Functional Applications

2018

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The term architectonics has its roots in the architectural and philosophical (as early as 1600s) literature that refers to "the theory of structure" and "the structure of theory", respectively. The concept of architectonics has been adapted to advance the field of molecular self-assembly and termed as molecular architectonics. In essence, the methodology of organizing molecular units in the required and controlled configurations to develop advanced functional systems for materials and biological applications comprises the field of molecular architectonics. This concept of designing noncovalent systems enables to focus on different functional aspects of designer molecules for biological and nonbiological applications and also strengthens our efforts toward the mastery over the art of controlled molecular self-assemblies. Programming complex molecular interactions and assemblies for specific functions has been one of the most challenging tasks in the modern era. Meticulously ordered molecular assemblies can impart remarkable developments in several areas spanning energy, health, and environment. For example, the well-defined nano-, micro-, and macroarchitectures of functional molecules with specific molecular ordering possess potential applications in flexible electronics, photovoltaics, photonic crystals, microreactors, sensors, drug delivery, biomedicine, and superhydrophobic coatings, among others. The functional molecular architectures having unparalleled properties are widely evident in various designs of Nature. By drawing inspirations from Nature, intended molecular architectures can be designed and developed to harvest various functions, as there is an inexhaustible resource and scope. In this Account, we present exquisite designer molecules developed by our group and others with an objective to master the art of molecular recognition and self-assembly for functional applications. We demonstrate the tailor-ability of molecular self-assemblies by employing biomolecules like amino acids and nucleobases as auxiliaries. Naphthalenediimide (NDI), perylenediimide (PDI), and few other molecular systems serve as functional modules. The effects of stereochemistry and minute structural modifications in the molecular designs on the supramolecular interactions, and construction of self-assembled zero-dimensional (OD), one-dimensional (1D), and two-dimensional (2D) nano- and microarchitectures like particles, spheres, cups, bowls, fibers, belts, helical belts, supercoiled helices, sheets, fractals, and honeycomb-like arrays are discussed in extensive detail. Additionally, we present molecular systems that showcase the elegant designs of coassembly, templated assembly, hierarchical assembly, transient self-assembly, chiral denaturation, retentive helical memory, self-replication, supramolecular regulation, supramolecular speciation, supernon linearity, dynamic pathway complexity, supramolecular heterojunction, living supramolecular polymerization, and molecular machines. Finally, we describe the molecular engineering pri...

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“…Concurrently, the chiral properties of the amino acid auxiliaries are manifested as a helical signature within these nanoarchitectures. 48,49 2.1.2. Amino Acid Chirality-Guided 2D Architectonics.…”

Section: D Architectures By Programmable Fabrication Strategiesmentioning

confidence: 99%

“…21,79,80 The molecular stability, predictable sequence specificity, molecular recognition characteristics, and the construction of regular and defined architectures through mutual templating of DNA and small functional molecules allow the custom design and engineering of a range of novel molecular and material architectures, which is also called templated DNA nanotechnology or DNA nanoarchitectonics. 79−82 We developed adenine (A) and thymine (T) functionalized NDIs, NDI-AA (48) and NDI-TT (49), and used them to template peptide nucleic acid (PNA) dimers, PNA-TT (50) and PNA-AA (51), respectively. 83 48 and 49 individually assemble into nanoribbon and nanobelt structures, respectively (Figure 6a,b), via hydrogen bonding and weak aromatic interactions.…”

Section: Chemistry Of Materialsmentioning

confidence: 99%

Two-Dimensional Molecular Architectonics through Controlled Noncovalent Interactions: Structure, Functional Properties, and Applications

Dinda,

Konar,

Govindaraju

2024

Chem. Mater.

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Fabrication of well-defined two-dimensional (2D) architectures employing organic or organic−inorganic hybrid molecular systems through bottom-up methodologies is a challenging task. The scheme of molecular architectonics aids in fabricating tailor-made 2D architectures through the controlled molecular assembly process. In this methodology, the controlled assembly characteristics are bestowed to functional organic cores by equipping them with appropriate biomolecular auxiliaries with inherent molecular recognition properties. The derived functional building blocks seamlessly integrate into two-dimensional macro-, micro-, and nanosheet structures through subtle noncovalent molecular assembly, coassembly, and templated assembly, ultimately showcasing a range of emergent functional properties and applications across various fields such as optoelectronics, catalysis, sensing, selfcleaning, drug delivery, and tissue engineering, among others. In this Perspective, we discuss auxiliary-guided 2D assembly architectures of functional cores through molecular assembly, coassembly, hierarchical assembly, tweezer-sandwich-inclusion (TIS) assembly, templated assembly, chiral assembly, complex dynamical assembly, self-sorted assembly, and the breath figure technique (BFT)-type assembly. The resulting tailor-made 2D architectures exhibit optoelectronic, conducting, chiro-optical, mechanical, sensor, host−guest recognition, and superhydrophobic properties.

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Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

Cited by 9 publications

References 50 publications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

Architectonics: Design of Molecular Architecture for Functional Applications

Two-Dimensional Molecular Architectonics through Controlled Noncovalent Interactions: Structure, Functional Properties, and Applications

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