Synthesis of N-Bridged Pyrido[4,3-d]pyrimidines and Self-Assembly into Twin Rosette Cages and Nanotubes in Organic Media

Download

10.1038s41598-018-34080-9.pdf

Date

2018-10-29

Author

Igci, Cansu
Karaman, Osman
Fan, Yiwen
Gonzales, Arthur A.
Fenniri, Hicham
Günbaş, Emrullah Görkem

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

85
views

85
downloads

Two N-bridged pyrido[4,3-d]pyrimidine derivatives were synthesized toward realization of a self-assembled bis-rosette cage, in organic media. Starting from commercially available ma lononitrile dimer and dimethyl 5-aminoisophthalate, the target molecules were synthesized in 11 steps using a convergent approach. The final bridged compounds were characterized by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The hierarchical self-assembly of the nanocages into rosette nanotubes and nanobundles was established by electron microscopy and molecular modelling studies.

Subject Keywords

Multidisciplinary, SOLID-STATE, ARCHITECTURE, COMPLEXES, HYDROGELS, MELAMINES

URI

https://hdl.handle.net/11511/47355

Journal

SCIENTIFIC REPORTS

DOI

https://doi.org/10.1038/s41598-018-34080-9

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of fused tetrazolone derivatives Ozcan, Sevil; Ekmekci, Zeynep; Mujde, Berk; Balcı, Metin (2013-01-01) New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazo...
Synthesis of conducting H-type polysiloxane-polypyrrole block copolymers Kalaycioglu, E; Toppare, Levent Kamil; Yagci, Y; Harabagiu, V; Pintela, M; Ardelean, R; Simionescu, BC (1998-08-30) Synthesis of a siloxane polymer with pyrrole end groups has been described. Electrochemical block polymerization of pyrrole through these end groups has been achieved. Characterization of the electrolytic products has been performed by means of scanning electron microscopy (SEM), differential scanning calorimetry (DSC), thermal gravimetry analysis (TGA) analyses and FT-IR studies. The effects of different dopant ions, namely, p-toluene sulfonic acid (PTSA) and tetrabutylammonium tetrafluoroborate (TBAFB), i...
SYNTHESIS OF BLOCK COPOLYMERS VIA ANION-TO-RADICAL TRANSFORMATION HAZER, B; CAKMAK, I; KUCUKYAVUZ, S; NUGAY, T (Elsevier BV, 1992-10-01) Synthesis of (methyl methacrylate)-styrene block copolymers was carried out using anion-to-radical transformation. For this purpose, living polystyryl anion, prepared by using a new anionic difunctional initiator, 1,5-di(2-(3,3-dimethyl butyl-1-lithio)naphthalene, was terminated by the addition of 4,4'-bromomethyl dibenzoyl peroxide. Polystyrene samples having peroxide terminal groups were then used as initiators in the polymerization of methyl methacrylate. Block copolymers were characterized by spectrosco...
Synthesis of New Thienylene Pyrrole Monomers and Their Electropolymerizations Eken, Serap; Carbas, Buket Bezgin; Akdağ, Akın; Önal, Ahmet Muhtar (The Electrochemical Society, 2014-01-01) In this study, four new 2,5-dithienylpyrroles (SNS) 1-(3-fluoro-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-FPTP), 1-(3-chlorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-ClPTP), 1-(3-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (m-BrPTP) and 1-(4-bromo-phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole (p-BrPTP) containing meta and para substituted benzene ring at the nitrogen atom were synthesized via Paal-Knorr condensation of 1,4-di(2-thienyl)-1,4-butanedione with corresponding halo-substituted anilines. The mon...
Synthesis of Indolizines by Dimerization of N-Propargylated Pyrroles via Allene Intermediates Kuzu, Burak; Gul, Sergen; Tan Uygun, Meltem; Mengeş, Nurettin; Balcı, Metin (2021-03-01) Ten different N-propargyl pyrrole derivatives having various substituents at the C-2 position were synthesized. These derivatives were converted into indolizine derivatives by the [2+2] cycloaddition reaction of pyrrole N-allene, forming in situ, by heating in PrOH in basic medium. The structures were characterized by NMR and X-ray crystallography. The N-propargylated derivatives smoothly underwent intermolecular cyclizations to produce indolizine derivatives in good yields. We proposed a radical mechanism ...

Citation Formats

C. Igci, O. Karaman, Y. Fan, A. A. Gonzales, H. Fenniri, and E. G. Günbaş, “Synthesis of N-Bridged Pyrido[4,3-d]pyrimidines and Self-Assembly into Twin Rosette Cages and Nanotubes in Organic Media,” SCIENTIFIC REPORTS, pp. 0–0, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47355.