Published in Issue 10-05-2018
How to Cite
Malah, T. E., & Nour, H. F. (2018). Synthesis of dendronic triazolo-pyridazinones and their self-assembly into nanofibers and nanorods. Journal of Nanostructure in Chemistry, 8(2 (June 2018). https://doi.org/10.1007/s40097-018-0262-9
HTML views: 41
PDF views: 107
Abstract
Abstract A series of first-, second-, and third-generation dendronic triazolo-pyridazinones were synthesized in good yields via the Cu I -catalyzed azide–alkyne cycloaddition reactions of 4,6-diphenyl-2-(prop-2-yn-1-yl)pyridazin-3(2 H )-one, possessing a terminal alkyne functional group with aromatic mono- and diazides with long alkyl and chiral glycol side-chain substituents. The chemical structures of the new compounds were characterized using different spectroscopic methods. The morphology of the dendrons was examined using the scanning electron microscope (SEM) analysis, which revealed the formation of highly ordered nanofiber and nanorod aggregations, directed by π-stacking interactions and van der Waals forces. Graphical abstractKeywords
- Dendron,
- Azide–alkyne cycloaddition,
- Self-assembly,
- Pyridazin-3(2H)-one,
- Nanofiber,
- Nanorod
References
- Busseron et al. (2013) Supramolecular self-assemblies as functional nanomaterials (pp. 7098-7140) https://doi.org/10.1039/c3nr02176a
- Zhan et al. (2017) Spatiotemporal control of supramolecular self-assembly and function 9(11) (pp. 10012-10018) https://doi.org/10.1021/acsami.7b00784
- Soto and Tiburcio (2016) Self-assembly of a supramolecular network with pseudo-rotaxane cross-linking nodes and its transformation into a mechanically locked structure by rotaxane formation (pp. 14149-14152) https://doi.org/10.1039/C6CC08151G
- Cheng et al. (2017) Dynamic supramolecular self-assembly: hydrogen bonding-induced contraction and extension of functional polymers (pp. 3294-3299) https://doi.org/10.1039/C7PY00684E
- Satapathy and Prasad (2016) Charge transfer modulated self-assembly in poly(aryl ether) dendron derivatives with improved stability and transport characteristics 8(39) (pp. 26176-26189) https://doi.org/10.1021/acsami.6b09175
- Sivadas et al. (2014) Supergelation via purely aromatic π–π driven self-assembly of pseudodiscotic oxadiazole mesogens 136(14) (pp. 5416-5423) https://doi.org/10.1021/ja500607d
- Xu and Zhao (2012) Electrostatic interactions versus van der Waals interactions in the self-assembly of dispersed nanodiamonds (pp. 16416-16421) https://doi.org/10.1039/c2jm32918b
- Kawano et al. (2018) Columnar liquid-crystalline macrocycles synthesized via metal ion-assisted self-assembly 57(7) (pp. 3913-3919) https://doi.org/10.1021/acs.inorgchem.8b00046
- Rolandi and Rolandi (2014) Self-assembled chitin nanofibers and applications (pp. 216-222) https://doi.org/10.1016/j.cis.2014.01.019
- Leung et al. (2016) Metal–metal and π–π interactions directed end-to-end assembly of gold nanorods 138(9) (pp. 2989-2992) https://doi.org/10.1021/jacs.6b01382
- Durmus et al. (2013) Synthesis of N-substituted pyrido[4,3-d]pyrimidines for the large-scale production of self-assembled rosettes and nanotubes 78(22) (pp. 11421-11426) https://doi.org/10.1021/jo4019792
- Putaux et al. (2017) Self-assembly of amphiphilic biotransesterified β-cyclodextrins: supramolecular structure of nanoparticles and surface properties 33(32) (pp. 7917-7928) https://doi.org/10.1021/acs.langmuir.7b01136
- Saikia and Pandey (2018) Polarity-induced surface recognition and self-assembly of noncanonical DNA nucleobases on h-BN monolayer (pp. 3915-3925) https://doi.org/10.1021/acs.jpcc.7b11993
- Rong et al. (2011) Self-assembly of viral particles (pp. 441-450) https://doi.org/10.1016/j.cocis.2011.09.001
- Jackman et al. (2015) Self-assembly formation of lipid bilayer coatings on bare aluminum oxide: overcoming the force of interfacial water 7(1) (pp. 959-968) https://doi.org/10.1021/am507651h
- Semerdzhiev et al. (2014) Self-assembly of protein fibrils into suprafibrillar aggregates: bridging the nano- and mesoscale 8(6) (pp. 5543-5551) https://doi.org/10.1021/nn406309c
- Teyssandier et al. (2016) Host-guest chemistry in two-dimensional supramolecular networks (pp. 11465-11487) https://doi.org/10.1039/C6CC05256H
- Cai et al. (2018) Potential- and concentration-dependent self-assembly structures at solid/liquid interfaces (pp. 3438-3443) https://doi.org/10.1039/C7NR08475G
- El Malah et al. (2012) Conformationally pre-organized and pH-responsive flat dendrons: synthesis and self-assembly at the liquid–solid interface (pp. 467-472) https://doi.org/10.1039/C1NR11434D
- Piot et al. (2009) Modulating large-area self-assembly at the solid–liquid interface by pH-mediated conformational switching 15(19) (pp. 4788-4792) https://doi.org/10.1002/chem.200802566
- Lee et al. (2014) Self-assembly of nanoparticle amphiphiles with adaptive surface chemistry 8(10) (pp. 9979-9987) https://doi.org/10.1021/nn504734v
- Guan et al. (2017) Aqueous self-assembly of hydrophobic macromolecules with adjustable rigidity of the backbone (pp. 5130-5136) https://doi.org/10.1039/C7SM01101F
- Mishra et al. (2017) Self-assembly of perylenediimide–single-strand-DNA conjugates: employing hydrophobic interactions and DNA base-pairing to create a diverse structural space 23(43) (pp. 10328-10337) https://doi.org/10.1002/chem.201700752
- Rubio et al. (2012) Interplay between hydrophilic and hydrophobic interactions in the self-assembly of a gemini amphiphilic pseudopeptide: from nano-spheres to hydrogels (pp. 2210-2212) https://doi.org/10.1039/c2cc17153h
- Zornik et al. (2011) Designing structural motifs for clickamers: exploiting the 1,2,3-triazole moiety to generate conformationally restricted molecular architectures 17(5) (pp. 1473-1484) https://doi.org/10.1002/chem.201002491
- El Malah et al. (2016) Anticancer evaluation of tris(triazolyl)triazine derivatives generated via click chemistry 69(8) (pp. 905-910)
- Ameen et al. (2015) Click chemistry based synthesis of novel architectures bearing sugar unit at the pyridothienopyrimidines 52(4) (pp. 1093-1098) https://doi.org/10.1002/jhet.2202
- Cadeddu et al. (2011) Modulating the self-assembly of rigid “clicked” dendrimers at the solid–liquid interface by tuning non-covalent interactions between side groups 47(38) (pp. 10578-10580) https://doi.org/10.1039/c1cc13099d
- Meudtner and Hecht (2008) Helicity inversion in responsive foldamers induced by achiral halide ion guests 47(26) (pp. 4926-4930) https://doi.org/10.1002/anie.200800796
- El Malah et al. (2012) Amphiphilic folded dendrimer discs and their thermosensitive self-assembly in water 18(19) (pp. 5837-5842) https://doi.org/10.1002/chem.201200414
- Zhang et al. (2015) Tuning soft nanostructures in self-assembled supramolecular gels: from morphology control to morphology-dependent functions 11(9–10) (pp. 1025-1038) https://doi.org/10.1002/smll.201402075
- Grynʹova et al. (2017) Charge transport in highly ordered organic nanofibrils: lessons from modelling https://doi.org/10.1039/C6TC04463H
- Zang et al. (2008) One-dimensional self-assembly of planar π-conjugated molecules: adaptable building blocks for organic nanodevices 41(12) (pp. 1596-1608) https://doi.org/10.1021/ar800030w
- Wu et al. (2016) Tunable morphology of spiropyran assemblies: from nanospheres to nanorods (pp. 3102-3106) https://doi.org/10.1002/asia.201601114
- Zhou et al. (2014) π–π stacking interaction induced the assembly of gold nanorods 148(3) (pp. 503-506) https://doi.org/10.1016/j.matchemphys.2014.08.060
- Wang et al. (2017) Alkyl bicarbamates supramolecular organogelators with effective selective gelation and high oil recovery from oil/water mixtures (pp. 178-187) https://doi.org/10.1016/j.chemosphere.2016.09.149
- Kocsis et al. (2018) Oriented chiral water wires in artificial transmembrane channels 4(3) https://doi.org/10.1126/sciadv.aao5603
- Islam and Sundararajan (2013) Self-assembly of a set of hydrophilic-solvophobic-hydrophobic coil-rod-coil molecules based on perylene diimide (pp. 21058-21069) https://doi.org/10.1039/c3cp52680a
- Wong et al. (2018) Formation of 1D infinite chains directed by metal–metal and/or π–π stacking interactions of water-soluble platinum(II) 2,6-bis(benzimidazol-2′-yl)pyridine double complex salts 140(2) (pp. 657-666) https://doi.org/10.1021/jacs.7b09770
- Baddi et al. (2016) Self-assembly of aromatic biscarbamate gelators: effect of spacer length on the gelation and rheology (pp. 637-649) https://doi.org/10.1007/s10971-016-4036-x
10.1007/s40097-018-0262-9