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[ CAS No. 18511-71-2 ] {[proInfo.proName]}

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Chemical Structure| 18511-71-2
Chemical Structure| 18511-71-2
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Product Citations

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Jonathan Taylor Yarranton ;

Abstract: lron(ll) polypyridyl chromophores are among one of the most promising earth-abundantalternatives to ruthenium-based complexes in the realms of photo-redox catalysis and solar energyharvesting. The biggest hurdle to their implementation is the sub-150 fs metal-to-ligand chargetransfer (MLCT)excited-state lifetime which limits their implementation in diffusion-imitedprocesses. The main way in which researchers have approached this problem is by attempting toinvert the ligand-field (LF) and MLCT manifolds by increasing the donor ability of the ligandsemployed. To better understand the destabilizing nature ofthe ligands employed, a series ofCo(ll)complexes were synthesized as an isoelectronic stand-in for Fe(ll) to measure the LF transitions ofvarious polypyridyl ligands as well as the first carbene ligand coordinated to Fe(ll) to detemmine therelevant ligand-field parameters and assess the splitting observed. These results indicate thatpolypyridyl complexes do not impose a strong enough LF to destabilize them above the MLCT. Tothat end, we synthesized a series of simple bis pyridinium-based polypyridyl ligands with increasedsigma-donor ability compared to the widely used carbene systems, achieving a MLCT lifetime of18 ps, a 2-fold increase from the first reported tetra-carbene system. A final thrust was to betterunderstand the unique MLCT manifold of [Fe(depp)2]+(where depp is 2,6-di(2.carboxypyridyl)pyridine) using symmetric n-substitutions. With this method, we were able tosynthetically deconvolute the MLCT spectrum and selectively enhance different transitions basedupon the substitution pattem. The computational insights gleaned can now guide new promisingligands in this family ofcomplexes.

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Kessinger, Matthew ; Soudackov, Alexander V. ; Schneider, Jenny , et al. DOI: PubMed ID:

Abstract: The reorganization energy (λ) for interfacial electron transfer (ET) and proton-coupled ET (PCET) from a conductive metal oxide (In2O3:Sn, ITO) to a surface-bound H2O oxidation catalyst was extracted from kinetic data measured as a function of the thermodn. driving force. Visible light excitation resulted in rapid excited-state injection (kinj > 108 s-1) to the ITO, which photo-initiated the two interfacial reactions of interest. The rate constants for both reactions increased with the driving force, -ΔG°, to a saturating limit, kmax, with rate constants consistently larger for ET than for PCET. Marcus-Gerischer anal. of the kinetic data provided the reorganization energy for interfacial PCET (0.90 ± 0.02 eV) and ET (0.40 ± 0.02 eV), resp. The magnitude of kmax for PCET decreases with pH, behavior that was absent for ET. Both the decrease in kmax and the larger reorganization energy for an unwanted competing PCET reaction from the ITO to the oxidized catalyst showcases a significant kinetic advantage for driving solar H2O oxidation at high pH. Computational anal. revealed a larger inner-sphere reorganization energy contribution for PCET than for ET arising from a more significant change in the Ru-O bond length for the PCET reaction. Extending the Marcus-Gerischer theory to PCET by including the excited electron-proton vibronic states and the proton donor-acceptor motion provided an apparent reorganization energy of 1.01 eV. The Marcus-Gerischer theory initially developed for ET can be reliably extended to PCET for quantifying and interpreting reorganization energies observed exptl.

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Product Details of [ 18511-71-2 ]

CAS No. :18511-71-2 MDL No. :MFCD00667763
Formula : C10H6Br2N2 Boiling Point : -
Linear Structure Formula :(C5H3BrN)2 InChI Key :KIIHBDSNVJRWFY-UHFFFAOYSA-N
M.W : 313.98 Pubchem ID :15569987
Synonyms :

Calculated chemistry of [ 18511-71-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.87
TPSA : 25.78 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 3.8
Consensus Log Po/w : 3.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.16
Solubility : 0.0219 mg/ml ; 0.0000697 mol/l
Class : Moderately soluble
Log S (Ali) : -3.06
Solubility : 0.273 mg/ml ; 0.00087 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.86
Solubility : 0.000437 mg/ml ; 0.00000139 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.15

Safety of [ 18511-71-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18511-71-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 18511-71-2 ]

[ 18511-71-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 18511-71-2 ]
  • [ 197223-39-5 ]
  • 4,4'-bis(3,5-di-tert-butylphenyl)-2,2'-bipyridine [ No CAS ]
  • 2
  • [ 17217-57-1 ]
  • [ 18511-71-2 ]
  • 3
  • [ 18511-71-2 ]
  • [ 68-12-2 ]
  • [ 99970-84-0 ]
YieldReaction ConditionsOperation in experiment
35% 7 was synthesized before by applying other methodologies.22,23 0.9 g of 6 (2.9 mmol) were dissolved in 25 cm3anhydrous diethyl ether and 25 cm3 anhydrous toluene undera nitrogen atmosphere at -78 C. Butyl lithium in hexane (5cm3, 2.5 mol/L)was added dropwise. The solutionwas stirredat -78 C for 90 min before 8.0 cm3 anhydrous dimethyl formamidewere added. The resulting solution was then stirredfor another 90 min at the same temperature. To stop the reaction50 cm3 2 N hydrochloric acid were added at -78 C andthe solution was then allowed to reach room temperature. Theorganic phase was separated and the aqueous phase was neutralizedwith diluted sodium hydroxide solution. A smooth white precipitate formed that was three times extracted withCH2Cl2. The solvent was evaporated under reduced pressureand a pale brown oil that solidified to a pale brown solid wasobtained. Yield: 35% (0.215 g, 1.01 mmol); M.p.: 194-196C, literature 192 C.24
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