Modulation of the structures and properties of bidipyrrin zinc complexes by introducing terminal α-methoxy groups

Kong, Jiahui; Li, Qizhao; Li, Minzhi; Li, Xin; Xu, Ling; Zhu, Weihua; Ågren, Hans; Xie, Yongshu

doi:10.1016/j.dyepig.2016.10.038

Cited by 10 publications

(2 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar strapped double helicates were then synthesized, and the exciton coupling between the multiple dipyrrin chromophores were observed (Maeda et al, 2013b ). The structure of the double helicates was also controlled by steric or electrostatic repulsion between the terminal substituents at the α positions of the bis(dipyrrin) ligands (Maeda et al, 2014 ; Kong et al, 2017 ).…”

Section: Self-assembly Of Discrete Supramolecular Architectures and Tmentioning

confidence: 99%

Functional Supramolecular Architectures of Dipyrrin Complexes

Matsuoka

Nabeshima

2018

Front. Chem.

View full text Add to dashboard Cite

Dynamic formation of self-assemblies from molecular components is a useful and efficient way to produce molecular and supramolecular architectures with sophisticated functions. The labile coordination bond and dynamic covalent bond as a reversible bond have often been used to create a well-organized supramolecular self-assembly. In order to realize sophisticated novel functions of the supramolecular self-assemblies, dipyrrin complexes have recently been employed as a functional unit and incorporated into the supramolecular architectures because of their outstanding properties and functions such as a high photostability and strong light absorption/emission. This review article summarizes recent development in functional supramolecular architectures of the dipyrrin complexes produced by coordination to a metal ion and dynamic covalent bond formation. We first describe the synthesis and unique functions of a series of discrete supramolecular architectures: helicates, macrocycles, and cages. The polymeric supramolecular self-assemblies with 1D, 2D, and 3D structures are then introduced as a functional infinite supramolecular architecture.

show abstract

Section: Self-assembly Of Discrete Supramolecular Architectures and Tmentioning

confidence: 99%

Functional Supramolecular Architectures of Dipyrrin Complexes

Matsuoka

Nabeshima

2018

Front. Chem.

View full text Add to dashboard Cite

show abstract

“…The successful preparation of such a quaterpyrrole prompted us to generalize this synthetic methodology, giving a straightforward access to substituted bipyrroles 3 bearing aromatic and unsaturated moieties at positions 5,5′ (Scheme ). The conjugated structure and the presence of the bipyrrolic moiety make these new molecules of interest in the design of metal ligands, − macrocyclic receptors, ,,− molecular electronics, light-emitting diodes, electrochromic devices, molecular wires, the preparation of conjugated low band gap polymers, − and polymer-based sensors. − …”

Section: Introductionmentioning

confidence: 99%

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

et al. 2017

View full text Add to dashboard Cite

The preparation and characterization of a family of stable 2,2'-bipyrroles substituted at positions 5 and 5' with thienyl, phenyl, TMS-ethynyl, and vinyl groups is reported herein. The synthesis of these new bipyrroles comprises three steps: formation of the corresponding 5,5'-unsubstituted bipyrrole, bromination, and Stille or Suzuki coupling. The best results in the coupling are obtained using the Stille reaction under microwave irradiation. The new compounds have been fully characterized by UV-vis absorption, fluorescence, and IR spectroscopies and cyclic voltammetry. X-ray single-crystal analysis of four of the synthesized bipyrroles indicates a trans coplanar geometry of the pyrrole rings. Furthermore, the substituents at positions 5,5' remain coplanar to the central rings. This particular geometry extends the π-conjugation of the systems, which is in agreement with a red-shifting observed for the λ of the substituted molecules compared to the unsubstituted bipyrrole. All of these new compounds display a moderate fluorescence. In contrast with unsubstituted bipyrroles, these bipyrroles are endowed with a high chemical and thermal stability and solubility in organic solvents.

show abstract

Visualizing Zn²⁺ in Living Whole Organism Artemia by a Natural Fluorimetric Intermediate Siderophore

et al. 2017

View full text Add to dashboard Cite

Aeruginic acid (H 2 L), a weakly fluorescent natural ionophore, was synthesized via one-pot mechanochemical grinding at room-temperature. This sulfur containing intermediate siderophore showed unique specificity towards Zn 2 + in 100% water at physiological pH even in presence of other challenging metal ions particularly, paramagnetic metal ions such as Fe 3 + , Co 2 + , Ni 2 + , and Cu 2 + . H 2 L also displayed a naked eye observable instant color change under UV light in presence of Zn 2 + , in aqueous solution and in solid phase as well. The receptor H 2 L with 49 nM limit of detection, upon excitation at 360 nm, reversibly binds one equivalent Zn 2 + as evidenced from Job's plot, ESI-MS, and 1 H NMR spectroscopy. Being fully water soluble, non-toxic, and permeable in nature, this natural ionophore can visualize Zn 2 + in the gastrointestinal tract of live whole brine shrimp Artemia. We are not aware of any report on bio-imaging of Zn 2 + in living organism.

show abstract

Modulation of the structures and properties of bidipyrrin zinc complexes by introducing terminal α-methoxy groups

Cited by 10 publications

References 45 publications

Functional Supramolecular Architectures of Dipyrrin Complexes

Functional Supramolecular Architectures of Dipyrrin Complexes

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

Visualizing Zn²⁺ in Living Whole Organism Artemia by a Natural Fluorimetric Intermediate Siderophore

Contact Info

Product

Resources

About

Modulation of the structures and properties of bidipyrrin zinc complexes by introducing terminal α-methoxy groups

Cited by 10 publications

References 45 publications

Functional Supramolecular Architectures of Dipyrrin Complexes

Functional Supramolecular Architectures of Dipyrrin Complexes

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

Visualizing Zn2+ in Living Whole Organism Artemia by a Natural Fluorimetric Intermediate Siderophore

Contact Info

Product

Resources

About

Visualizing Zn²⁺ in Living Whole Organism Artemia by a Natural Fluorimetric Intermediate Siderophore