151237-05-7Relevant articles and documents
Distance Matters: Biasing Mechanism, Transfer of Asymmetry, and Stereomutation in N-Annulated Perylene Bisimide Supramolecular Polymers
Aragó, Juan,Calbo, Joaquín,Cerdá, Jesús,Crassous, Jeanne,Doncel-Giménez, Azahara,Martínez, Manuel A.,Ortí, Enrique,Rodríguez, Rafael,Sánchez, Luis
, p. 13281 - 13291 (2021/09/03)
The synthesis of two series of N-annulated perylene bisimides (PBIs), compounds 1 and 2, is reported, and their self-assembling features are thoroughly investigated by a complete set of spectroscopic measurements and theoretical calculations. The study co
An electron-deficient tris(triazole)-based discotic liquid crystal that exhibits fast electron transport
Bala, Indu,De, Joydip,Dhingra, Shallu,Gupta, Santosh Prasad,Pal, Santanu Kumar,Pandey, Upendra Kumar
, p. 5628 - 5632 (2021/05/17)
In this study, a C3-symmetric star-shaped discotic mesogen has been reported based on an electron-deficient tris(triazole) central rigid core functionalized with three peripheral trialkoxyphenyl units. The mesogen exhibits an enantiotropic columnar hexagonal (Colh) phase that can sustain over a significant temperature range. When used in space-charge limited current (SCLC) devices, it showed ambipolar charge transport behavior with high electron mobility (μe) of 1.61 × 10-2 cm2 V-1 s-1 at ambient temperature. The finding is sufficiently significant to warrant their use in organic electronic devices.
High Hole Mobility and Efficient Ambipolar Charge Transport in Heterocoronene-Based Ordered Columnar Discotics
De, Joydip,Bala, Indu,Gupta, Santosh Prasad,Pandey, Upendra Kumar,Pal, Santanu Kumar
, p. 18799 - 18805 (2019/11/21)
Heterocoronene, a new redox-active core fragment, is utilized for the synthesis of room-temperature columnar discotic liquid crystals (DLCs). Three wedge-shaped side chains having different lengths of alkyl tails are introduced at the periphery of the het
Self-assembly and solid-state polymerization of butadiyne derivatives with amide and trialkoxyphenyl groups
Kikuchi, Kohei,Tatewaki, Yoko,Okada, Shuji
, p. 298 - 305 (2017/05/10)
Three butadiyne derivatives with amide and tri(dodecyloxy)-phenyl (TDP) groups were synthesized, and four solidification methods were applied to obtain their self-assembling states in various conditions. The solids obtained were characterized by the solid-state polymerization behaviors, stretching vibration wavenumbers of N-H bonds of amide groups, powder X-ray diffraction, the thermal behaviors, and scanning electron microscope (SEM) observations. We found that all compounds had at least two polymorphs. Property differences between two polymorphs depended on the compounds. Two compounds showed clear differences in UV-vis spectra of the photo-polymerized solids, i.e., the polydiacetylene (PDA) structure, and irregularly polymerized form, or two PDA structures. The remaining compound showed the same PDA absorption but the monomer melting points were different. All compounds gave the gels in various organic solvents because of the molecular design with amide and TDP groups. SEM observation clarified the relationship between gel appearance and the nanostructures.
Generation of liquid crystallinity from a Td-symmetry central unit
Sayed, Sayed Mir,Lin, Bao-Ping,Yang, Hong
, p. 6148 - 6156 (2016/07/26)
A series of new columnar liquid crystals containing an adamantane central unit with its four bridgehead positions partially or fully decorated with different numbers (1-4) of 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups were designed and investigated carefully to explore the structure-property correlations. The molecular structures and mesomorphic properties of the DLCs were characterized by 1H-NMR, 13C-NMR, IR, UV-vis, POM, DSC and XRD. It was found that the mesophase symmetry and thermal stability were extremely dependent on the structures of the adamantane derivatives. No mesophase was observed for the 1-adamantanecarboxylic acid derivative ADLC1, while two different mesophases were observed for ADLC2, a 1,3-disubstituted derivative functionalized with two 3,4,5-tris(dodecyloxy)phenyl carbamoyl groups at two symmetric bridgehead positions. At lower temperature ADLC2 exhibited a rectangular columnar phase, which switched to a square columnar phase possessing a wide temperature range. Similarly, a hexagonal columnar mesophase was observed for the bridgehead trisubstituted adamantane molecule ADLC3. Interestingly, the fully bridgehead-functionalized 1,3,5,7-tetrasubstituted adamantane compound ADLC4 completely lost liquid crystallinity.
Supramolecular assembly of isocyanorhodium(i) complexes: An interplay of rhodium(i)···rhodium(i) interactions, hydrophobic-hydrophobic interactions, and host-guest chemistry
Chan, Alan Kwun-Wa,Wong, Keith Man-Chung,Yam, Vivian Wing-Wah
, p. 6920 - 6931 (2015/06/16)
A series of tetrakis(isocyano)rhodium(I) complexes with different chain lengths of alkyl substituents has been found to exhibit a strong tendency toward solution state aggregation upon altering the concentration, temperature and solvent composition. Temperature- and solvent-dependent UV-vis absorption studies have been performed, and the data have been analyzed using the aggregation model to elucidate the growth mechanism. The aggregation is found to involve extensive Rh(I)···Rh(I) interactions that are synergistically assisted by hydrophobic-hydrophobic interactions to give a rainbow array of solution aggregate colors. It is noted that the presence of three long alkyl substituents is crucial for the observed cooperativity in the aggregation. Molecular assemblies in the form of nanoplates and nanovesicles have been observed in the hexane-dichloromethane solvent mixtures, arising from the different formation mechanisms based on the alkyl chain length of the complexes. Benzo-15-crown-5 moieties have been incorporated for selective potassium ion binding to induce dimer formation and drastic color changes, rendering the system as potential colorimetric and luminescent cation sensors and as building blocks for ion-controlled supramolecular assembly.
An unusual stacking transformation in liquid-crystalline columnar assemblies of clicked molecular propellers with tunable light emissions
Kim, Jinhee,Cho, Sung,Cho, Byoung-Ki
, p. 12734 - 12739 (2015/03/30)
The columnar liquid-crystalline (LC) and fluorescence properties of three-dimensional molecular propellers based on tetraphenylethylene is reported. X-ray scattering studies reveal an unusual transition from a rectangular (Colrec) to a hexagona
Synthesis of novel supramolecular triads bearing a H-bonded perylene bisimide core
Rajan, Yesudoss Christu,Shellaiah, Muthaiah,Huang, Ching-Ting,Lin, Hsin-Chieh,Lin, Hong-Cheu
, p. 7926 - 7931 (2012/10/08)
Two novel hydrogen-bonded (H-bonded) triads consisting of triazine derivatives complexed with a perylene bisimide core were synthesized and characterized. NMR, UV/vis, and fluorescence spectra of these supramolecular triads confirmed the formation of stro
Synthesis and characterization of supramolecular optically active bisamides derived from amino acids
Shanker,Shankar Rao,Krishna Prasad,Yelamaggad
supporting information; scheme or table, p. 6528 - 6534 (2012/09/07)
The synthesis and phase transitional behaviour of three pairs of enantiomeric supramolecular hexacatenar liquid crystals (LCs) derived from natural α-amino acids such as l/d-alanine, l/d-leucine and l/d-valine are described. Their preparation with high enantiomeric purity was accomplished by condensing optically active (amino acid residue containing) trialkoxy amines with a 3,4,5-trialkoxy cinnamic acid core using a peptide coupling reagent namely, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate (HBTU). The mesomorphic behaviour of these self-complementing mesogens was ascertained by polarising optical microscopy, differential scanning calorimetry and X-ray diffraction. The compounds exhibit columnar (Col) phase over a wide thermal range. Particularly, a pair of enantiomers derived from l/d-leucine residues notably stabilize hexagonal Col (Colh) phase over a wide temperature range of -5 °C to 180 °C. Circular dichroism (CD) and FTIR studies suggest the chiral (helical) organization of mesogens within the columns through intermolecular hydrogen bonding; thus, these enantiomers represent one of the rarely reported examples of LCs exhibiting supramolecular Colh phase at room temperature. The gelation studies reveal the ability of these bisamides to form stable supramolecular gels in ethanol caused through H-bonding interactions.
Supramolecular functionalization of single-walled carbon nanotubes (SWNTs) with dithieno[3,2- b:2′,3′-d ]pyrrole (DTP) containing conjugated polymers
Imin, Patigul,Imit, Mokhtar,Adronov, Alex
, p. 9138 - 9145 (2012/04/18)
Fluorene and dithieno[3,2-b:2′,3′-d]pyrrole (DTP) containing conjugated polymers, {2,7-[9,9-didodecylfluorene]-alt-2,6-[N-dodecyldithieno(3, 2-b:2′,3′-d)pyrrole]} (PF-DTP1) and {2,7-[9,9-didodecylfluorene]- alt-2,6-[N-3,4,5(n-dodecyloxy)phenyldithieno(3,2-b:2′,3′-d)pyrrole]} (PF-DTP2), have been successfully synthesized using Suzuki polycondensation. These polymers possess excellent thermal stability with decomposition temperatures over 365 °C under Ar. The introduction of soluble side chains on the DTP units and incorporation with soluble dialkyl-substituted fluorene resulted in highly soluble polymers with novel optoelectronic properties. The supramolecular complex formation of these DTP containing polymers with single-walled carbon nanotubes (SWNTs) has been studied, and it was found that these polymers can form strong supramolecular polymer-nanotube assemblies and produce stable complexes in solution. UV-vis-NIR absorption, photoluminescence excitation (PLE), and Raman spectroscopy were used for the characterization and identification of the nanotube species that are present in THF solution. The strong nanotube emission was observed from individual SWNTs even after removal of excess free polymer by filtration and washing. On the basis of these two polymers, it was found that the interactions with the SWNT surface are more strongly dictated by the polymer backbone than the side chain, though further studies may be warranted.
