Structural Studies of the Self-Assemblies Created with Dipyrrins

Shin, Ji‐Young; Patrick, Brian O.; Hahn, Jae-Ryang; Dolphin, David

doi:10.5012/bkcs.2010.31.04.1004

Cited by 14 publications

(7 citation statements)

References 30 publications

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“…Two different orientations of the Mn(III) complexes are analyzed (SI, Figure S12). Both are taken from the crystal structure with refcode IZEVUF (tris(2-((pentafluorophenyl)(2 H -pyrrol-2-ylidene)methyl)-1 H -pyrrolato) manganese(III)) . In the first orientation (Figure a), the aromatic rings participate in PILO (the distance between the ring centers is 5.64 Å) and in a pair of the F/F interactions (both with the distance of 2.85 Å).…”

Section: Resultsmentioning

confidence: 99%

“…Electrostatic potential maps of the Mn(III) complex, extracted from the crystal structure with refcode IZEVUF (a), and 2-((pentafluorophenyl)(2 H -pyrrol-2-ylidene)methyl)-1 H -pyrrole (b), used for the evaluation of the coordination effects on interactions of the fluorine atom bound to the aromatic groups with the T-shaped geometries.…”

Section: Resultsmentioning

confidence: 99%

“…Both are taken from the crystal structure with refcode IZEVUF (tris(2-((pentafluorophenyl)-(2H-pyrrol-2-ylidene)methyl)-1H-pyrrolato) manganese-(III)). 27 In the first orientation (Figure 13a), the aromatic rings participate in PILO (the distance between the ring centers is 5.64 Å) and in a pair of the F/F interactions (both with the distance of 2.85 Å). The strength of interaction between these two complexes is −3.40 kcal/mol.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Benazzouz

Rakić

Trišović

et al. 2021

Crystal Growth & Design

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Coordination effects have been considered through the most common interactions in the crystal structures of fluoro compounds (C−H/F and F/F interactions). The supramolecular profile of these effects is based on quantum-chemical calculations for the assessment of the interaction strength and electrostatic potential maps, which provide a qualitative insight into the examined effect. Coordination of aliphatic fluorides leads to an increase of the negative potential of the F atoms, and, hence, an increase in the hydrogen-bonding acceptor ability (strengthening of C−H/F interactions) and a weakening of the F/F interactions, due to an increase in repulsive interactions between the F atoms. There is no significant change in the potential of the F atoms due to coordination of C 6 -aromatic fluorides, as in the case of aliphatic ones. This results in slight changes in the strengths of the C−H/F and F/F interactions (coupled with parallel interaction at large offsets, PILO), in a noticeable enhancement of stacking interactions, as well as in a significant enhancement of interactions involving the π-system (F/π and C−H/π interactions). It has also been shown that a decrease in the charge of the metal ions leads to a decrease in the negative potential of the F atom and also that the nature of the metal ion has a significant influence on the value of the potential of the F atoms.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Benazzouz

Rakić

Trišović

et al. 2021

Crystal Growth & Design

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“…In addition, the BODIPYs are applied to laser dyes, photovoltaics, electrochemical luminescent materials, bio-imaging, and photodynamic therapy (Ortiz et al, 2010 ; Benstead et al, 2011 ; Awuah and You, 2012 ; Boens et al, 2012 ; Kamkaew et al, 2013 ; Bessette and Hanan, 2014 ; Ni and Wu, 2014 ; Singh and Gayathri, 2014 ; Zhao et al, 2015 ; Antina et al, 2016 ). These attractive functions of BODIPY and other dipyrrin complexes encouraged us and other researchers to incorporate the dipyrrin complexes into the frameworks of the supramolecular self-assemblies (Shin et al, 2010 ; Antina et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

Functional Supramolecular Architectures of Dipyrrin Complexes

Matsuoka

Nabeshima

2018

Front. Chem.

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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.

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“…However, the bis (iminiopyridine) compounds with CuBr 2 and ZnBr 2 differ significantly in molecular structure . Also compounds of dipyrromethenes with Cu(II) and Zn(II) halides containing CuCl 4 and ZnCl 4 tetrahedra have no isomorphous structures . Thus, there is not a general rule allowing a prediction if Cu(II) and Zn(II) compounds of identical chemical formula will be isomorphous or not.…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds

et al. 2017

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X‐ray diffraction structure of two new bis [1‐methyl‐3‐(methoxycarbonylmethyl) benzimidazolium]2+ [CuBr4]2− and [ZnBr4]2− compounds has been determined. Zn‐crystal is monoclinic with perfect Td symmetry of the ZnBr4 tetrahedron, whereas the Cu‐compound is orthorhombic with D2d symmetry of CuBr4 tetrahedron. The difference in these structures is described as due to the static Jahn‐Teller effect. Vibrational spectroscopy (1800–3200 cm−1) identified hydrogen bond network. NIR‐UV‐Vis spectra (5000–50000 cm−1) are dominated by ligand‐to‐metal bands with d‐d transition contribution. EPR results (Q‐band) analyzed in terms of the MO‐theory showed a very strong delocalization of unpaired electron density on ligands accompanied by the Cu(II) 4pz orbital contribution. This effect is partially compensated by charge transfer transitions to the EPR g‐factor.

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Structural Studies of the Self-Assemblies Created with Dipyrrins

Cited by 14 publications

References 30 publications

Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Functional Supramolecular Architectures of Dipyrrin Complexes

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds

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Structural Studies of the Self-Assemblies Created with Dipyrrins

Cited by 14 publications

References 30 publications

Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Supramolecular Perspective of Coordination Effects on Fluorine Interactions

Functional Supramolecular Architectures of Dipyrrin Complexes

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]2+ [CuBr4]2− and [ZnBr4]2− Compounds

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Product

Resources

About

Syntheses, Crystal Structures and Spectroscopic Studies of Bis[1‐methyl‐3‐(methoxycarbonylmethyl)‐benzimidazolium]²⁺ [CuBr₄]²⁻ and [ZnBr₄]²⁻ Compounds