Chiral Transcription and Retentive Helical Memory: Probing Peptide Auxiliaries Appended with Naphthalenediimides for Their One‐Dimensional Molecular Organization

Makam, Pandeeswar; Avinash, M. B.; Govindaraju, T.

doi:10.1002/chem.201200197

Cited by 66 publications

(65 citation statements)

References 69 publications

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“…In this case, although the handedness of the nanohelix did not change, the packing of the acceptor is in the opposite direction of the nanohelix, therefore, we observed inversion of the supramolecular chirality localized on the BPEA. It is interesting that the guest (acceptor) molecules can carry on either the same or the opposite chiral packing against the host (donor) chiral matrices, which have been widely reported in supramolecular-assembled chiral systems5565758. This phenomenon has been explained to the different molecular packing between host chiral donors and guest achiral acceptors according to the theory of exciton-coupled circular dichroism59.…”

Section: Discussionmentioning

confidence: 99%

Chirality and energy transfer amplified circularly polarized luminescence in composite nanohelix

et al. 2017

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Transfer of both chirality and energy information plays an important role in biological systems. Here we show a chiral donor π-gelator and assembled it with an achiral π-acceptor to see how chirality and energy can be transferred in a composite donor–acceptor system. It is found that the individual chiral gelator can self-assemble into nanohelix. In the presence of the achiral acceptor, the self-assembly can also proceed and lead to the formation of the composite nanohelix. In the composite nanohelix, an energy transfer is realized. Interestingly, in the composite nanohelix, the achiral acceptor can both capture the supramolecular chirality and collect the circularly polarized energy from the chiral donor, showing both supramolecular chirality and energy transfer amplified circularly polarized luminescence (ETACPL).

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Section: Discussionmentioning

confidence: 99%

Chirality and energy transfer amplified circularly polarized luminescence in composite nanohelix

et al. 2017

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“…[31][32][33][34][35] In this context, biomolecules such as amino acids and their derivatives are particularly appealing due to their remarkable metal chelating nature, aqueous solubility, specific molecular recognition, and ability to self-assemble into functional, complex and highly ordered molecular systems and nanomaterials through various noncovalent interactions. [36][37][38][39][40][41] Herein we report an easy and one step synthesis of PDI derivative 1 with L-DOPA functionality as a well-known receptor at the N-imide positions, and assembly-disassembly modulated detection of Fe 3+ and Cu 2+ metal ions. It was presumed that incorporation of L-DOPA would render the aqueous solubility to PDI derivative 1 and consequently a fluorescence probe in aqueous medium could be established.…”

Section: Introductionmentioning

confidence: 99%

Assembly Modulation of PDI Derivative as a Supramolecular Fluorescence Switching Probe for Detection of Cationic Surfactant and Metal Ions in Aqueous Media

Dwivedi

Makam

Govindaraju

2014

ACS Appl. Mater. Interfaces

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We report an amphiphilic perylene diimide (1), a bimolecular analog of l-3,4-dihydroxyphenylalanine (L-DOPA), as a reversible fluorescence switching probe for the detection and sensing of cationic surfactants and Fe(3+)/Cu(2+) in an aqueous media respectively by means of host-guest interactions driven assembly and disassembly of 1. Photophysical studies of 1, going from dimethyl sulfoxide (DMSO) (State-I) to pure aqueous medium (State-II), suggested the formation of self-assembled aggregates by displaying very weak fluorescence emission along with red shifted broad absorption bands. Interestingly, the cationic surfactant cetyltrimethylammonium bromide (CTAB) could disassemble 1 in miceller conditions by restoring bright yellow fluorescence and vibronically well-defined (Franck-Condon progressions A0-0/A0-1 ≈ 1.6) absorption bands of 1 over other neutral and anionic surfactants (State-III). Owing to the metal chelating nature of L-DOPA, 1 was able to sense Fe(3+) and Cu(2+) among a pool of other metal ions by means of fluorescence switching off state, attributed to metal interaction driven assembly of 1 (State-IV). Such metallosupramolecular assemblies were found to reverse back to the fluorescence switching on state using a metal ion chelator, diethylenetriaminepentaacetic acid (DTPA, State-III), further signifying the role of metal ions toward assembly of 1. Formation of assembly and disassembly could be visualized by the diminished and increased yellow emission under green laser light. Further, the assembly-disassembly modulation of 1 has been extensively characterized using infrared (IR), mass spectrometry, microscopy and dynamic light scattering (DLS) techniques. Therefore, modulation of the molecular self-assembly of PDI derivative 1 in aqueous media (assembled state, State-II) by means of host-guest interactions provided by micellar structures of CTAB (disassembled state, State-III), metal ion (Fe(3+) and Cu(2+)) interactions (assembled state, State-IV) and metal ion sequestration using DTPA (disassembled state, State-III) is viewed as a supramolecular reversible fluorescence switching off-on probe for cationic surfactant CTAB and Fe(3+)/Cu(2+).

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“…have reported the formation of 1D fibers, spheres, sheets [17] and 1D nanobelts. [18] In 2005, Matile and coworkers designed, synthesized and characterized a synthetic ion channel using aromatic electron donor-acceptor interactions. [19] Their design utilized a rigid-rod NDI-NDI off-set architecture that underwent a conformational change and opened to form a barrel-stave ion channel in response to intercalation of DAN monomer between the NDI-NDI units.…”

Section: Introductionmentioning

confidence: 99%

More than Meets the Eye: Conformational Switching of a Stacked Dialkoxynaphthalene–Naphthalenetetracarboxylic diimide (DAN–NDI) Foldamer to an NDI–NDI Fibril Aggregate

Peebles

Piland

Iverson

2013

Chemistry A European J

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The thermally induced conformational switching of a stacked dialkxoynaphthalene- naphthalenetetracarboxylic diimide (DAN-NDI) amphiphilic foldamer to an NDI-NDI fibril aggregate is described. The aggregated fibril structures were explored by UV-Vis, CD, AFM and TEM. Our findings indicate that the aromatic DAN-NDI interactions of the original foldamer undergoes transformation to a fibrillar assembly with aromatic NDI-NDI stacked interactions. These structural insights could help inform new molecular designs and increase our understanding of the fibrillar assembly and aggregation process in aqueous solution.

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Chiral Transcription and Retentive Helical Memory: Probing Peptide Auxiliaries Appended with Naphthalenediimides for Their One‐Dimensional Molecular Organization

Cited by 66 publications

References 69 publications

Chirality and energy transfer amplified circularly polarized luminescence in composite nanohelix

Chirality and energy transfer amplified circularly polarized luminescence in composite nanohelix

Assembly Modulation of PDI Derivative as a Supramolecular Fluorescence Switching Probe for Detection of Cationic Surfactant and Metal Ions in Aqueous Media

More than Meets the Eye: Conformational Switching of a Stacked Dialkoxynaphthalene–Naphthalenetetracarboxylic diimide (DAN–NDI) Foldamer to an NDI–NDI Fibril Aggregate

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