Self-assembly of oligomeric linear dipyrromethene metal complexes

Miao, Qing; Shin, Ji‐Young; Patrick, Brian O.; Dolphin, David

doi:10.1039/b820461f

Cited by 60 publications

(43 citation statements)

References 11 publications

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“…5). 20 A small number of heteroleptic bis(dipyrrinato)metal complexes have been reported by Cohen, 25 and Radecka, 26,27 and Dolphin, 28 first example of a heteroleptic zinc(II) complex that contains two types of dipyrrinato ligands with drastic differences in their electronic structures: one derived from either of the homoleptic complexes 6 and 7. Fig.…”

Section: Heteroleptic Bis and Tris(dipyrrinato)metal Complexesmentioning

confidence: 99%

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New aspects in bis and tris(dipyrrinato)metal complexes: bright luminescence, self-assembled nanoarchitectures, and materials applications

et al. 2015

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Dipyrrins serve as monovalent bidentate ligand molecules that coordinate to various cations. Their BF 2 complexes, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene and its derivatives (BODIPYs), exhibit excellent photostability, strong light absorption, and high fluorescence quantum yield, thereby encouraging their application in various fields, e.g., as biological and biomedical fluorescent markers. Dipyrrin may also accept a wide variety of metal ions spontaneously. However, dipyrrin metal complexes have been disregarded from materials science research. This review article summarizes recent progress in bis(dipyrrinato)metal(II) and tris(dipyrrinato)metal(III) complexes from the viewpoint of materials chemistry. Section 2 describes a series of efforts aimed to realize intense luminescence superior to or comparable with that of BODIPYs. The spontaneous coordination of these complexes enables them to construct self-assembled nanoarchitectures, such as supramolecules and coordination polymers that form one-dimensional nanowires, two-dimensional nanosheets, and metal-organic frameworks. Section 3 describes such alluring molecular superstructures. Section 4 discusses potential applications based on these nanoarchitectures, such as thermoelectric and photoelectric conversion. aimed to realize intense luminescence superior to or comparable with that of BODIPYs. Section 3 discusses the selfassembly of bis and tris(dipyrrinato)metal complexes, which results in the formation of alluring nanoarchitectures, such as supramolecules and coordination polymers giving rise to onedimensional nanowires, two-dimensional nanosheets, and metal-organic frameworks (MOFs) and porous coordination polymers (PCPs). Section 4 describes potential applications based on these nanoarchitectures. Pursuit of bright luminescenceA plain BODIPY shows intense absorption and bright fluorescence at approximately 500 nm, which are derived from the 1 π-π * transition of the dipyrrinato ligand. 5-16 The absorption and fluorescence may be redshifted upon the introduction of substituents on the dipyrrinato ligand, covering the region 500-900 nm. BODIPYs are good fluorophores even in polar solvents such as water. In sharp contrast, dipyrrin metal complexes have long been believed to be non-luminescent or weakly luminescent. This drawback seriously reduces the value of dipyrrinato-metal complexes in applications in which they serve, for example, as photosensitizers. In this section, the authors concentrate on efforts to improve the luminescent ability of bis and tris(bisdipyrrinato)metal complexes. For comprehensive knowledge on the whole types of luminescent dipyrrinato-metal complexes (i.e. mono(dipyrrinato)metal complexes with ancillary ligands other than dipyrrins), please see a comprehensive review article contributed by Baudron. 2

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Section: Heteroleptic Bis and Tris(dipyrrinato)metal Complexesmentioning

confidence: 99%

“…28 Single strands of bis(dipyrrinato)zinc(II) coordination polymers were synthesized and isolated by Sakamoto and Nishihara (Fig. 14).…”

Section: One-dimensional Coordination Polymersmentioning

confidence: 99%

New aspects in bis and tris(dipyrrinato)metal complexes: bright luminescence, self-assembled nanoarchitectures, and materials applications

et al. 2015

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“…The NMR spectra of the metal complexes 6-9 exhibit signals over a large chemicalshift range or completely disappeared due to the paramagnetism of the metal centers while the diamagnetic Zn complexes 5 shows typical chemical shifts in their NMR spectrum. As reported in previously, [31][32][33] the optical spectra of the metal complexes showed strong absorption bands newly appearing along with metal complexation. Similarly, the optical spectrum of the trivalent metal complexes 8 and 9 are also dramatically changed from that of the ligand.…”

Section: Mnmentioning

confidence: 51%

Structural Studies of the Self-Assemblies Created with Dipyrrins

Shin¹,

Patrick²,

Hahn³

et al. 2010

Bulletin of the Korean Chemical Society

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Three-dimensional superstructures of unique self-assemblies generated by exploring the conformational flexibility of various dipyrromethenes through creation of hydrogen-bonds with metal-halide anions are reported and the conformational diversity is thoroughly described in the solid and solution states by X-ray diffraction analysis and variable temperature NMR spectroscopy. The tetrahedral or octahedral structures of their precursors, various metal-dipyrromethene complexes, are also reported, based on the crystallographic data. STM images of the self-assemblies observed on graphite surfaces present interesting arrangements and appear as tubular bunches.

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“…The synthesis of this complex has been described elsewhere. 22 The structure and purity of each compound was confirmed by 1 H and…”

Section: Methodsmentioning

confidence: 99%

Ring and Volcano Structures Formed by a Metal Dipyrromethene Complex

Miao¹,

Shin²,

Dolphin³

et al. 2014

Bulletin of the Korean Chemical Society

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Dichloromethane liquid droplets containing a cobalt dipyrromethene trimer deposited on a graphite surface were found to form coffee ring, toroid ring, or volcano dot structures due to the redistribution of the solute during solvent evaporation. The shapes and size distributions of the ring structures depended on the drying temperature. The shape differences were attributed to the fact that the solvent evaporation rate controlled the self-assembly process that yielded the coffee stain and pinhole structures.

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Self-assembly of oligomeric linear dipyrromethene metal complexes

Abstract: BF(2) capped dipyrrin dimers were synthesized and have been used to terminate oligomerization to form a series of controlled length oligomers; the crystal structures of the metal complexes were investigated and correlations between the structures and optical properties were established.

Cited by 60 publications

References 11 publications

New aspects in bis and tris(dipyrrinato)metal complexes: bright luminescence, self-assembled nanoarchitectures, and materials applications

New aspects in bis and tris(dipyrrinato)metal complexes: bright luminescence, self-assembled nanoarchitectures, and materials applications

Structural Studies of the Self-Assemblies Created with Dipyrrins

Ring and Volcano Structures Formed by a Metal Dipyrromethene Complex

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