Brilliant reversible luminescent mechanochromism of silver(i) complexes containing o-bis(diphenylphosphino)benzene and phosphinesulfide

Tsukuda, Toshiaki; Kawase, Marina; Dairiki, Ayumi; Matsumoto, Kenji; Tsubomura, Taro

doi:10.1039/b921111j

Cited by 116 publications

(76 citation statements)

References 31 publications

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“…[8][9][10] It has been suggested that mechanical stimuli-responsive color and luminescence changes are often associated with a metastable state that is maintained at ambient condition but switched to the initial state upon heat or solvent-induced recrystallization. [4,12] Several metal complexes with silver(I), [32] copper(I), [33] gold(I), [14a, 34-36] zinc(II), [37] or platinum(II) [17c, 38] ions have been reported to exhibit distinct mechanoluminescence or triboluminescence induced by mechanical grinding, crushing, rubbing, extruding, or pressing, which is always correlated with formation/disruption of an intermolecular metal-metal contact [33,34,36] [32,38] or a change in molecular conformation. [35] We are interested in stimuli-responsive color and luminescence changes in bis(s-acetylide)platinum(II) complexes with 5,5'-bis(trimethylsilylethynyl)-2,2'-bipyridine (Me 3 SiC CbpyC C-SiMe 3 ).…”

Section: Introductionmentioning

confidence: 99%

Vapor‐ and Mechanical‐Grinding‐Triggered Color and Luminescence Switches for Bis(σ‐fluorophenylacetylide) Platinum(II) Complexes

Zhang

et al. 2011

Chemistry A European J

190

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Square-planar bis(σ-fluorophenylacetylide) platinum(II) complexes [Pt(Me(3)SiC≡CbpyC≡C-SiMe(3))(C≡CC(6)H(4)F)(2)] (C≡CC(6)H(4)F-2 for 2, C≡CC(6)H(4)F-3 for 3, and C≡CC(6)H(4)F-4 for 4; Me(3)SiC≡CbpyC≡CSiMe(3)=5,5'-bis(trimethylsilylethynyl)-2,2'-bipyridine) were prepared and were characterized by spectroscopic and luminescence studies, and X-ray crystallography. The color and luminescence of crystalline complex 3 is specifically sensitive to CHCl(3) vapor to afford 140-180 nm of luminescence vapochromic redshift, which is useful for specific detection of CHCl(3) vapor. Complex 4 displays selective luminescence vapochromic properties to CH(2)Cl(2) and CHCl(3) vapors with a luminescence vapochromic shift response of ca. 150-200 nm. Interestingly, complexes 2-4 exhibit reversible, and naked-eye perceivable, mechanical stimuli-responsive color and luminescence changes. When solid species 2-4 are crushed gently or ground, the crystalline state is converted to an amorphous phase. Meanwhile, bright yellow-orange luminescence in the crystalline species is converted to dark red under UV light irradiation with 100-160 nm of mechanochromic shift response. A vapochromic or mechanochromic cycle was monitored by dynamic variations in emission spectra and X-ray diffraction (XRD) patterns. The halohydrocarbon vapor- or mechanical-grinding-triggered color and luminescence switches are most likely correlated to a shorted intermolecular Pt-Pt distance as that revealed in vapochromic species 4·0.5 CH(2)Cl(2) by X-ray crystallography, thus leading to an increased contribution from intermolecular Pt-Pt interaction as demonstrated by DTF computational studies.

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Section: Introductionmentioning

confidence: 99%

Vapor‐ and Mechanical‐Grinding‐Triggered Color and Luminescence Switches for Bis(σ‐fluorophenylacetylide) Platinum(II) Complexes

Zhang

et al. 2011

Chemistry A European J

190

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“…Some examples are sensors for volatile organic compounds (VOCs) 3–37. Furthermore, a new concept of sensing motion and changes in mechanical force has recently been proposed, luminescence mechanochromism and tribochromism 38–47. Vapo‐ and mechanoluminescent complexes in the solid state show reversible emission‐color changes in the visible or near‐infrared regions.…”

Section: Introductionmentioning

confidence: 99%

“…Vapo‐ and mechanoluminescent complexes in the solid state show reversible emission‐color changes in the visible or near‐infrared regions. These spectral shifts, as responses of VOCs or mechanical force, generally originate from molecular conformation changes in the solid state, e.g., metal–metal distance,3–22, 40, 41, 43–45 coordination of VOCs,23–26 trapped VOCs in a crystal lattice,27–29 weak noncovalent interactions (π–π interaction, hydrogen bonding, CH–π interactions),8, 11, 19, 20, 26, 30–36, 40, 43, 47 isomerization involving polymer complexes and oligomers,37 and planarization of the conjugated ligand 46. Up to now, a number of linearly‐coordinated Au I systems have been reported as vapoluminescent compounds3, 6, 9 or mechanoluminescent materials 39–41.…”

Section: Introductionmentioning

confidence: 99%

Vapochromic and Mechanochromic Tetrahedral Gold(I) Complexes Based on the 1,2‐Bis(diphenylphosphino)benzene Ligand

Osawa

Kawata

Igawa

et al. 2010

Chemistry A European J

118

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Tetrahedral gold(I) complexes containing the diphosphane ligand (dppb=1,2-bis(diphenylphosphino)benzene), [Au(dppb)(2)]X [X=Cl (1), Br (2), I (3), NO(3) (4), BF(4) (5), PF(6) (6), B(C(6)H(4)F-4)(4) (7)], and the ethanol and methanol adducts of complex 4, 8, and 9, were prepared to analyze their unique photophysical properties. These complexes are classified into two categories on the basis of their crystal structures. In Category I, the complexes (1-5) have relatively-small counter anions and two dppb ligands are symmetrically coordinated to the central Au(I) atom, and display an intense blue phosphorescence. Alternatively, the complexes (6-9) in Category II have large counter anions and two dppb ligands asymmetrically coordinated to Au(I) atom, and display a yellow or yellow orange phosphorescence. The difference in the phosphorescence color of the complexes between the Category I and II is ascribed to the change in the structure of the cationic moiety in the complex. According to DFT calculations, the symmetry reduction caused by the large counter anion of the complex in Category II gives the destabilization of HOMO (σ*) levels, leading to the red-shift of the emission peak. We have demonstrated that the symmetry reductions are responsible for the phosphorescence color alteration caused by external stimuli (volatile organic compounds and mechanical grinding).

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“…have found important applications as fluorescent materials in organic light-emitting diodes (OLEDs). 62, 63 Application of dppben in industrial processes dates back to 1966 when a number of phosphine ligands in the reaction of butadiene with ethylene were shown to afford 1,4-hexadiene. Dppben was the most efficient phosphine in the process.…”

Section: Carbon-carbon and Carbon-heteroatom Bond-forming Reactions Bmentioning

confidence: 99%

1,2-Bis(diphenylphosphino)benzene

Csákÿ¹,

Molina²

2011

Encyclopedia of Reagents for Organic Synthesis

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Brilliant reversible luminescent mechanochromism of silver(i) complexes containing o-bis(diphenylphosphino)benzene and phosphinesulfide

Cited by 116 publications

References 31 publications

Vapor‐ and Mechanical‐Grinding‐Triggered Color and Luminescence Switches for Bis(σ‐fluorophenylacetylide) Platinum(II) Complexes

Vapor‐ and Mechanical‐Grinding‐Triggered Color and Luminescence Switches for Bis(σ‐fluorophenylacetylide) Platinum(II) Complexes

Vapochromic and Mechanochromic Tetrahedral Gold(I) Complexes Based on the 1,2‐Bis(diphenylphosphino)benzene Ligand

1,2-Bis(diphenylphosphino)benzene

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