Pyrene-Naphthalene Diimide-Pyrene Triad의 합성 및 물성에 대한 연구
Synthesis and Property of Pyrene-Naphthalene Diimide-Pyrene Triad
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In this study, we presented a newly synthesized pyrene-naphthalene diimide (NDI)-pyrene triad. The optical and structural properties were examined using various characterization techniques. A donor-acceptor-donor triad molecule exhibited a strong charge transfer, though there existed neither intramolecular nor intermolecular hydrogen bonding sites, due to the formation of preferential complementary complex between pyrene and NDI. Powder XRD measurement revealed a sharp and distinctive X-ray patterns, indicating the presence of microcrystalline-like structure. POM images showed anisotropic fingerprint texture similar to that of cholesteric phase, and SEM images showed numerous columnar structures with length of 1 to 10μm. Above observation clearly demonstrated that π-complementary NDI-pyrene interactions in the traid was strong enough to form columnar aggregates in the long range.
Abstract
In this study, we presented a newly synthesized pyrene-naphthalene diimide (NDI)-pyrene triad. The optical and structural properties were examined using various characterization techniques. A donor-acceptor-donor triad molecule exhibited a strong charge transfer, though there existed neither intramolecular nor intermolecular hydrogen bonding sites, due to the formation of preferential complementary complex between pyrene and NDI. Powder XRD measurement revealed a sharp and distinctive X-ray patterns, indicating the presence of microcrystalline-like structure. POM images showed anisotropic fingerprint texture similar to that of cholesteric phase, and SEM images showed numerous columnar structures with length of 1 to 10μm. Above observation clearly demonstrated that π-complementary NDI-pyrene interactions in the traid was strong enough to form columnar aggregates in the long range.
참고문헌 (20)
- A. Das, "Luminescent Invertible Polymersome by Remarkably Stable Supramolecular Assembly of Naphthalene Diimide(NDI) π-System", Macromolecules, 46(1), pp.3939~ (2013)
- 김형주, "Synthesis of Chemosensor Based on Pyrene and Study for Its Sensing Properties Toward Fluoride Ion", 한국염색가공학회지, 25(3), pp.153~158 (2013), 한국염색가공학회[DOI]
- 김형주, "Electrochemical Study on Energy Potential Levels with Pyrene Molecule", 한국염색가공학회지, 25(3), pp.159~164 (2013), 한국염색가공학회[DOI]
- X. Q. Li, "Donor-Acceptor Interaction-Mediated Arrangement of Hydrogen Bonded Dimers", Tetrahedron, 60(37), pp.8275~ (2004)
- S. Burattini, "A Healable Supramolecular Polymer Blend based on Aromatic π-π Stacking and Hydrogen-Bonding Interactions", J. of the American Chemical Society, 132(34), pp.12051~ (2010)
- H. Kar, "Two-Component Gelation and Morphology Dependent Conductivity of a Naphthalene-Diimide(NDI) p-System by Orthogonal Hydrogen Bonding", Chemical Communications, 49(39), pp.4220~ (2013)
- A. Bheemaraju, "Effect of Side Chains on Charge Transfer in Quaterthiophene-Naphthalene Diimide based Donor-Bridge-Acceptor Dyads", J. of Macromolecular Science, Part A:Pure and Applied Chemistry, 48(12), pp.986~ (2012)
- Rotaxane, "Organic Letters", 2010, 1728~
- F. B. L. Cougnon, "Exploring the Formation Pathways of Donor-Acceptor Catenanes in Aqueous Dynamic Combinatorial Libraries", J. of the American Chemical Society, 133(9), pp.3198~ (2011)
- T. Murase, "Pairwise Selective Formation of Aromatic Stacks in a Coordination Cage", J. of the American Chemical Society, 132(23), pp.7864~ (2010)
- J. M. Mativetsky, "Self-Assembly of a Donor-Acceptor Dyad Across Multiple Length Scales: Functional Architectures for Organic Electronics", Advanced Functional Materials, 19(15), pp.2486~ (2009)
- M. Mizusaki, "Interactions of Amphiphilic Polyelectrolytes and Neutral Polymeric Micelles: A Study by Nonradiative Energy Transfer", Langmuir, 15(23), pp.8090~ (1999)
- J. Duhamel, "Side-Chain Dynamics of an a-Helical Polypeptide Monitored by Fluorescence", J. of the American Chemical Society, 125(42), pp.12810~ (2003)
- B. W. Greenland, "Design, Synthesis and Computational Modelling of Aromatic Tweezer-Molecules as Models for Chain-Folding Polymer Blends", Tetrahedron, 64(36), pp.8346~ (2007)
- M. R. Molla, "Self-Sorted Assembly in a Mixture of Donor and Acceptor Chromophores", Chemistry-A European J, 16(33), pp.10084~ (2010)
- N. S. S. Kumar, "Evidence of Preferential p-Stacking: A Study of Intermolecular and Intramolecular Charge Transfer Complexes", Chem. Commun, 46(30), pp.5464~ (2010)
- M. D. Gujrati, "Luminescent Charge Transfer Complexes: Tuning Emission in Binary Fluorophore Mixtures", Langmuir, 27(11), pp.6554~ (2011)
- M. R. Molla, "Self-Assembly of Carboxylic Acid Appended Naphthalene Diimide Derivatives with Tunable Luminescent Color and Electrical Conductivity", Chemistry-A European J, 20(3), pp.760~ (2014)
- cinnoline, Tetraazapyrene, Phenanthrene, and Pyrene: The Effect of Heteroatom and Substitution Pattern on Phase Stability, "J. of Materials Chemistry", 2007, 1399~
- M. B. Avinash, "Molecular Assembly of Amino Acid Interlinked, Topologically Symmetric, p-Complementary Donor-Acceptor-Donor Triads", Beilstein J. of Organic Chemistry, 9, pp.1565~ (2013)