<i>fac</i>-Tricarbonyl Rhenium(I) Azadipyrromethene Complexes

Partyka, David V.; Deligonul, Nihal; Washington, Marlena P.; Gray, Thomas

doi:10.1021/om900552e

Cited by 57 publications

(52 citation statements)

References 48 publications

(67 reference statements)

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“…The bond lengths and angles around the rhenium centres and the fac-Re(CO) 3 unit are comparable between the two structures (Table 2), and also with those found in closely related structures of fac-[Re(ADPM)(L)(CO) 3 ] [where L = pyridine (py), tert-butylisonitrile and tetrahydrotiophene (THT)] (Partyka et al, 2009). Nevertheless, the Re1-C39 bond is significantly shorter in (3) than in (2).…”

Section: Figuresupporting

confidence: 74%

Twofac-tricarbonylrhenium(I) azadipyrromethene (ADPM) complexes: ligand-substitution effect on crystal structure

et al. 2015

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The crystal structures of fac-(acetonitrile-κN)(2-{[3,5-bis(4-methoxyphenyl)-2H-pyrrol-2-ylidene-κN(1)]amino}-3,5-bis(4-methoxyphenyl)-1H-pyrrol-1-ido-κN(1))tricarbonylrhenium(I)-hexane-acetonitrile (2/1/2), [Re(C36H30N3O4)(CH3CN)(CO)3]·0.5C6H14·CH3CN, (2), and fac-(2-{[3,5-bis(4-methoxyphenyl)-2H-pyrrol-2-ylidene-κN(1)]amino}-3,5-bis(4-methoxyphenyl)-1H-pyrrol-1-ido-κN(1))tricarbonyl(dimethyl sulfoxide-κO)rhenium(I), [Re(C36H30N3O4)(C2H6OS)(CO)3], (3), at 150 K are reported. Both complexes display a distorted octahedral geometry, with a fac-Re(CO)3 arrangement and one azadipyrromethene (ADPM) chelating ligand in the equatorial position. One solvent molecule completes the coordination sphere of the Re(I) centre in the remaining axial position. The ADPM ligand shows high flexibility upon coordination, while retaining its π-delocalized nature. Bond length and angle analyses indicate that the differences in the geometry around the Re(I) centre in (2) and (3), and those found in three reported fac-Re(CO)3-ADPM complexes, are dictated mainly by steric factors and crystal packing. Both structures display intramolecular C-H...N hydrogen bonding. Intermolecular interactions of the Csp(2)-H...π and Csp(2)-H...O(carbonyl) types link the discrete monomers into extended chains.

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Section: Figuresupporting

confidence: 74%

Twofac-tricarbonylrhenium(I) azadipyrromethene (ADPM) complexes: ligand-substitution effect on crystal structure

et al. 2015

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“…[36][37][38][39][40][41][42][43][44][45][46] Typically, complexes are formed under mild rt conditions in THF with t-butoxide or DIPEA as base. This points to an ever expanding future for these complexes not just for their own inherent properties but also for catalysis and material applications.…”

Section: 35mentioning

confidence: 99%

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

2016

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Azadipyrromethenes were first described over 70 years ago as blue pigments, but now are rapidly emerging as a compound class with highly desirable near infrared photophysical properties. Since the turn of the century several routes to azadipyrromethenes have been developed and numerous post-synthesis derivatizations have allowed for their exploitation in both biological and material sciences. The relative ease of access to specifically designed derivatives is now allowing their use in multiple technological formats from real-time fluorescence imaging, to solar energy materials, to optoelectronic devices and many more. In this review we have highlighted the synthetic component of this story as it is the ability to generate the designer azadipyrromethene that opens the door to exciting applications.

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“…[8] The conjugated psystem in these ligands endows the complexes with favorable optical properties, such as intense absorption with high molar absorption coefficients (e > 10 4 m À1 cm À1 ) and moderate-to-quantitative fluorescence quantum yields. [9][10] Among these compounds, boron complexes, such as 4,4-difluoro-4bora-3a,4a-diaza-s-indacenes (abbreviated as BODIPYs), hold great promise as ideal sensitizers owing to their favorable properties. [11] These systems exhibit strong absorption in the range 500-600 nm, as well as significant fluorescence quantum yields and high photostability.…”

Section: Introductionmentioning

confidence: 99%

“…Keywords: aza-BODIPY · dyes/ pigments · photooxidation · singlet oxygen · triplet excited states tracted less attention and have only been studied in the last decade. [10,[13][14][15][16] With the objective of developing new and efficient photosensitizers that exhibit near-infrared absorption, we designed a new series of aza-BODIPY derivatives and investigated their photophysical properties under different conditions. Interestingly, the triplet excited state, as well as the efficiencies of singlet-oxygen generation, of these aza-BODIPY derivatives could be successfully tuned from about 1 % to 86 % through judicial heavy-atom substitution.…”

Section: Introductionmentioning

confidence: 99%

Aza‐BODIPY Derivatives: Enhanced Quantum Yields of Triplet Excited States and the Generation of Singlet Oxygen and their Role as Facile Sustainable Photooxygenation Catalysts

Adarsh

Shanmugasundaram

Avirah

et al. 2012

Chemistry A European J

158

127

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A new series of aza-BODIPY derivatives (4 a-4 c, 5 a,c, and 6 b,c) were synthesized and their excited-state properties, such as their triplet excited state and the yield of singlet-oxygen generation, were tuned by substituting with heavy atoms, such as bromine and iodine. The effect of substitution has been studied in detail by varying the position of halogenation. The core-substituted dyes showed high yields of the triplet excited state and high efficiencies of singlet-oxygen generation when compared to the peripheral-substituted systems. The dye 6 c, which was substituted with six iodine atoms on the core and peripheral phenyl ring, showed the highest quantum yields of the triplet excited state (Φ(T) =0.86) and of the efficiency of singlet-oxygen generation (Φ(Δ) =0.80). Interestingly, these dyes were highly efficient as photooxygenation catalysts under artificial light, as well as under normal sunlight conditions. The uniqueness of these aza-BODIPY systems is that they are stable under irradiation conditions, possess strong red-light absorption (620-680 nm), exhibit high yields of singlet-oxygen generation, and act as efficient and sustainable catalysts for photooxygenation reactions.

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fac-Tricarbonyl Rhenium(I) Azadipyrromethene Complexes

Abstract: Rhenium(I) complexes of azadipyrromethene ligands are reported; three have been characterized crystallographically. The free ligands and their metallo-complexes undergo reductive electrochemistry. Red-light absorption results from optically allowed transitions to a ligand-localized LUMO.

Cited by 57 publications

References 48 publications

Twofac-tricarbonylrhenium(I) azadipyrromethene (ADPM) complexes: ligand-substitution effect on crystal structure

Twofac-tricarbonylrhenium(I) azadipyrromethene (ADPM) complexes: ligand-substitution effect on crystal structure

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

Aza‐BODIPY Derivatives: Enhanced Quantum Yields of Triplet Excited States and the Generation of Singlet Oxygen and their Role as Facile Sustainable Photooxygenation Catalysts

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