Synthesis, spectroscopy, electrochemistry, and coordination chemistry of substituted phosphine sulfides and selenides

Breshears, Andrew T.; Behrle, Andrew C.; Barnes, Charles L.; Laber, Charles H.; Baker, Gary A.; Walensky, Justin R.

doi:10.1016/j.poly.2015.07.008

Cited by 18 publications

(22 citation statements)

References 53 publications

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“…Since acharge transfer was excluded the strong deformation of the anthracenep lane is probably responsible for the unusual unstructured, broad and red-shifted emission in solutiona sw as also assumed earlier. [33] The recently reported positional isomerso f5 revealed an early planar anthracene core and therefore at ypical vibronic emission band, which wasa lso less red-shifted. [40] The low quantum yields can be explained by ap hotoinduced electron transfer (PET) from the sulfur lone pairs towards the anthracene psystem,w hich leads to as trong fluorescence quenching.…”

Section: Photophysical Propertiesmentioning

confidence: 95%

“…The 31 P-NMR signals of the resulting thiophosphoranyl anthracenes are shifteddownfield to about + 34 ppm, whichisslightly different compared to other diphenyl thiophosphoranyl substituted arenes. [33] They usually exhibit chemical shifts in an arrow range of 42-43 ppm (Table S1).…”

Section: Synthesismentioning

confidence: 99%

“…Moreover,astrong distortion of the anthraceneplane is observed resulting in an along C9•••C10 bent butterfly orientation with the wings towards the sulfur atom, which has been observed for 5 in previous studies. [31][32][33] The grade of that butterfly arrangementi sq uantified by the folding angle a,w hich is the intersecting angle between two planes throught he outer four C-atoms( C1 to C4 and C5 to C8) ( Figure 2a). In order to investigate, whether the different orientation of the phenylg roups in 1 and 5 is ac rystal packing effect or inherent to the structures themselves, theoretical geometry optimisationsw ere carried out at the D3-B3LYP//def2-TZVP level.…”

Section: Structural Propertiesmentioning

confidence: 99%

“…[31,32] Later,f urtherd ipheny(thiophosphoranyl) substituted polyaromatic hydrocarbonsh ave been reporteda nd especially the anthracenyld erivative revealed interesting structural features like as trongb ending of the anthracene core, which was assumed to influence the spectroscopic properties. [33] For af urther investigation we synthesized and characterised ac lass of thiophosphoranyl anthracenes in the present study to investigate the structure-property-relationship especially in terms of solid-state luminescence.…”

Section: Introductionmentioning

confidence: 99%

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Analysis of Solid‐State Luminescence Emission Amplification at Substituted Anthracenes by Host–Guest Complex Formation

Schillmöller

Ruth

Herbst‐Irmer

2020

Chemistry A European J

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Small robust organic molecules showing solidstate luminescence are promising candidates foro ptoelectronic materials. Herein, we investigate as eries of diphenylphosphanyl anthracenes [9-PPh 2-10-R-(C 14 H 8)] and their sulfur oxidised analogues.T he oxidation causes drastic changes in the molecular structurea st he new orientation of the bulky (S)PPh 2 substituent inducesastrongb utterfly bent structure of the anthracenec ore, which triggersastrong bathochromic shift resulting in ag reen solid-state fluorescence. As the emission properties changeo nly slightly upon aggregation the origin of the emission is attributed to at ypical monomer fluorescence. The host-guest complexes of [9-(S)PPh 2-10-Ethyl-(C 14 H 8)] with four basic arenes reveal an emissione nhancement up to five-times higherq uantum yields comparedt ot he pure host. Less interchromophoric interactions and ar estriction of intramolecular motion within the hostm olecules due to fixation by weak CÀH•••p interactions with the co-crystallised arene are responsible for that emission enhancement.

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Section: Photophysical Propertiesmentioning

confidence: 95%

Section: Synthesismentioning

confidence: 99%

Section: Structural Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Analysis of Solid‐State Luminescence Emission Amplification at Substituted Anthracenes by Host–Guest Complex Formation

Schillmöller

Ruth

Herbst‐Irmer

2020

Chemistry A European J

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“…The IR spectrum of dithiocarbamate showed bands at respectively, these two bands indicates the thioureide group was coordinated with Hg +2 and Zn +2 ions through the sulfur atoms as bridge and chelate bidentate [15,16]. The spectra of complexes (3)(4)(5)(6)(7)(8)(9)(10) showed the v(C-S) and v(C=S) within (985-995) and (1066-1072) cm -1 range respectively, and displayed a new bands at (1427-1433) cm -1 , (501-540) cm -1 , (1182) cm -1 and (694)cm -1 range assigned to v(P-Ph), v(P-C) [17][18][19][20][21][22][23][24][25][26][27][28], v(P=O) [29] and v(P=S) [30] indicating the phosphine ligand was coordinated with the metal ions. s: strong, m: medium, w : weak 3.3 NMR spectra The 1 H and 31 P chemical shifts are listed in Table (3).…”

Section: Spectroscopic Studies 321 Infrared Spectramentioning

confidence: 99%

Synthesis and characterization of new mixed ligand complexes of Zn (II) and Hg (II) with dithiocarbamate and phosphines

Kareem¹,

Jirjes²

2020

Tikrit J. Pure Sci.

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Complexes of the type [M (Et2DTC)2]2 [M= Zn(1) or Hg(2)] were prepared from the reaction of mercury acetate or zinc acetate with sodium diethyldithiocarbamate trihydrate (NaEt2DTC.3H2O) in (1:2) molar ratio (metal: ligand) in mixture of MeOH and H2O as a solvent. Treatment equal molar of (1) or (2) with diphosphine ligands {where diphos: bis (diphenylphosphino) methane (dppm), 1,2-bis (diphenylphosphino) ethane (dppe) and 1,3-Bis (diphenylphosphino) propane (dppp)} afforded complexes of the type [Zn(Et2DTC)2(dppeO)] (3); [Zn(Et2DTC)2(dpppS)] (4a); [Zn(Et2DTC)2(dppp)] (4b); [Hg(Et2DTC)2(dppm)] (6a); [Hg(Et2DTC)2(µ-dppm)]2(6b); [Hg(Et2DTC)2(dppe)](7) and [Hg(Et2DTC)2(dppp)](8), or with two moles of triphenylphosphine (PPh3) afforded a complexes of the type [M(κ1-Et2DTC)2(PPh3)2] (5a, 9a) and [M(κ2-Et2DTC)2(PPh3)2] (5b, 9b) {M= Zn, Hg}. The prepared complexes were fully characterized by different technics such as IR, NMR (1H and 31P) spectroscopy, elemental analysis, and molar conductivity. Characterization data showed that the (Et2DTC) ligand in all of the prepared complexes was coordinated with metal through the sulfur atoms of CSS- group. The geometry of the complexes (1-9) were tetrahedral around the Zn(II) and Hg(II) ions, except isomers 5b and 9b are octahedral geometry. . http://dx.doi.org/10.25130/tjps.25.2020.011

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Phosphorus‐Directed Rhodium‐Catalyzed C−H Arylation of 1‐Pyrenylphosphines Selective at the K‐Region

et al. 2021

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CÀ H arylation of 1-pyrenylphosphine derivatives catalyzed by rhodium and directed by a diphenylphosphino group is selectively achieved at the K-region, i. e. 4-, 5-, 9-, or 10-position of the pyrene moiety. This peri CÀ H activation/arylation of pyrenes using (hetero)aryl bromide coupling partners tolerates both electron-donating and electron-withdrawing groups on the arene, and provides isolated yields of products between 25% to 90%, including from bulky polyaromatic bromoarene substrates. We achieved investigations directed at the formation and reactivity of pertinent intermediate species in this CÀ H arylation reaction. The P-ligand coordination at rhodium was established using 31 P NMR and XRD analysis, and we isolated five-membered rhodacycles as intermediates to the directed CÀ H functionalization. The data obtained overall supported the occurrence of a cationic rhodium catalytic process. We further described the access to a large class of pyrenylphosphine ligands and their selenated derivatives. Phosphine selenation allows to rapidly estimate from 1 J P = Se values the basic character of the ligand in the perspective of their use for coordination. Accordingly, linear P-coordinated Au(I) gold complexes were isolated, in addition to the variously coordinated Rh(III) complexes. The present methodology significantly extends the scope of polyaromatics that are functionalizable at the K-Region by direct CÀ H activation, beyond smaller-sized naphtalenes and aminopyrenes.

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Synthesis, spectroscopy, electrochemistry, and coordination chemistry of substituted phosphine sulfides and selenides

Cited by 18 publications

References 53 publications

Analysis of Solid‐State Luminescence Emission Amplification at Substituted Anthracenes by Host–Guest Complex Formation

Analysis of Solid‐State Luminescence Emission Amplification at Substituted Anthracenes by Host–Guest Complex Formation

Synthesis and characterization of new mixed ligand complexes of Zn (II) and Hg (II) with dithiocarbamate and phosphines

Phosphorus‐Directed Rhodium‐Catalyzed C−H Arylation of 1‐Pyrenylphosphines Selective at the K‐Region

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