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Biomimetic molecular organization of naphthalene diimide in the solid state: tunable (chiro-) optical, viscoelastic and nanoscale properties

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dc.contributor.author Pandeeswar, M.
dc.contributor.author Khare, Harshavardhan
dc.contributor.author Ramakumar, Suryanarayanarao
dc.contributor.author Govindaraju, T.
dc.date.accessioned 2017-02-21T08:56:25Z
dc.date.available 2017-02-21T08:56:25Z
dc.date.issued 2014
dc.identifier.citation Pandeeswar, M; Khare, H; Ramakumar, S; Govindaraju, T, Biomimetic molecular organization of naphthalene diimide in the solid state: tunable (chiro-) optical, viscoelastic and nanoscale properties. RSC Advances 2014, 4 (39) 20154-20163, http://dx.doi.org/10.1039/c3ra47257d en_US
dc.identifier.citation RSC Advances en_US
dc.identifier.citation 4 en_US
dc.identifier.citation 39 en_US
dc.identifier.issn 2046-2069
dc.identifier.uri https://libjncir.jncasr.ac.in/xmlui/10572/2487
dc.description Restricted Access en_US
dc.description.abstract The interfacing of aromatic molecules with biomolecules to design functional molecular materials is a promising area of research. Intermolecular interactions determine the performance of these materials and therefore, precise control over the molecular organization is necessary to improve functional properties. Herein we describe the tunable biomimetic molecular engineering of a promising n-type organic semiconductor, naphthalene diimide (NDI), in the solid state by introducing minute structural mutations in the form of amino acids with variable Ca-functionality. For the first time we could achieve all four possible crystal packing modes, namely cofacial, brickwork, herringbone and slipped stacks of the NDI system. Furthermore, amino acid conjugated NDIs exhibit ultrasonication induced organogels with tunable visco-elastic and temperature responsive emission properties. The amino acid-NDI conjugates self-assemble into 0D nanospheres and 1D nanofibers in their gel state while the ethylamine-NDI conjugate forms 2D sheets from its solution. Photophysical studies indicated the remarkable influence of molecular ordering on the absorption and fluorescence properties of NDIs. Interestingly, the circular dichroism (CD) and X-ray diffraction (XRD) studies revealed the existence of helical ordering of NDIs in both solution and solid state. The chiral amino acids and their conformations with respect to the central NDI core are found to influence the nature of the helical organization of NDIs. Consequently, the origin of the preferential handedness in the helical organization is attributed to transcription of chiral information from the amino acid to the NDI core. On account of these unique properties, the materials derived from NDI-conjugates might find a wide range of future interdisciplinary applications from materials to biomedicine. en_US
dc.description.uri http://dx.doi.org/10.1039/c3ra47257d en_US
dc.language.iso English en_US
dc.publisher Royal Society of Chemistry en_US
dc.rights @Royal Society of Chemistry, 2014 en_US
dc.subject Chemistry en_US
dc.subject Helical Organic Nanotubes en_US
dc.subject Aromatic Interactions en_US
dc.subject Charge-Transfer en_US
dc.subject Functionalized Naphthalenediimides en_US
dc.subject Rational Design en_US
dc.subject Pi Interactions en_US
dc.subject Electronics en_US
dc.subject Chirality en_US
dc.subject Polymers en_US
dc.subject Recognition en_US
dc.title Biomimetic molecular organization of naphthalene diimide in the solid state: tunable (chiro-) optical, viscoelastic and nanoscale properties en_US
dc.type Article en_US


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