Reaction products of dichlorodiorganostannanes with sodium in liquid ammonia: In-situ investigations with 119Sn NMR spectroscopy and usage as intermediates for the synthesis of tetraorganostannanes

Trummer, Markus; Zemp, J.; Sax, Cédric; Smith, Paul; Caseri, Walter

doi:10.1016/j.jorganchem.2011.05.001

Cited by 12 publications

(17 citation statements)

References 51 publications

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“…Lower molecular weight (10 3 Da) polystannanes were more recently obtained by Caseria nd co-workers from the Wurtz coupling of dialkyltin dichlorides in liquid ammonia. [8,12] Electrochemical coupling of dialkyltin dichlorides to low molecular weightp olymers (10 3 Da) has also been demonstrated by Okano et al. [13,14] In 2015, Harrypersada nd Foucher described the preparation of moderate molecular weight (10 4 -10 5 Da) alternating polystannanes from the condensation polymerization of diaryl or dialkyl tin dihydridesw ith appropriately chosen dialkyltind iamides.…”

Section: Introductionmentioning

confidence: 92%

“…Earlier work by Molloy and co‐workers had also shown that high molecular weight (10 5 Da) polystannanes can be prepared through a low‐temperature (60 °C) Na‐mediated Wurtz coupling of dialkyltin dichlorides or alkylaryltin dibromides in toluene in the presence of 15‐crown‐5. Lower molecular weight (10 3 Da) polystannanes were more recently obtained by Caseri and co‐workers from the Wurtz coupling of dialkyltin dichlorides in liquid ammonia . Electrochemical coupling of dialkyltin dichlorides to low molecular weight polymers (10 3 Da) has also been demonstrated by Okano et al.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Readily Modified Poly(aryl)(alkoxy)stannanes by use of Hypercoordinated Sn Monomers

Pau

D’Amaral

Lough

et al. 2018

Chemistry A European J

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The synthesis and solid‐state molecular structures of two dichlorido(aryl)(alkyl) tin compounds, 5 and 8, both key intermediates to tunable polystannane architectures, are reported. The materials were further investigated by single‐crystal XRD and a DFT analysis of their preferential “open and closed” geometries. Conversion of said compounds to their dihydride analogues was undertaken, followed by their application as monomers for polystannane polymer synthesis. The properties of two asymmetrical polystannanes prepared by transition‐metal‐catalyzed dehydropolymerization of dihydrido(aryl)alkylstannanes (6 and 9) were investigated. The first product was the structurally simple, modest molecular weight, semi‐crystalline light‐ and moisture‐stable polystannane 10 with NMR (119Sn) evidence of prominent Sn←O hypercoordination along the polymer backbone. The second was the lower molecular weight, tosylated four‐coordinate polystannane 11 with no evidence of hypercoordination. Differential scanning calorimetry (DSC) of polymer 10 revealed a reversible semi‐crystalline nature, whereas an amorphous character was detected for polymer 11. Polystannane 10 was also found to be exceptionally stable to both moisture and light (>6 months) and a promising candidate for the design of readily modified (i.e., tunable) polystannane materials.

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Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Readily Modified Poly(aryl)(alkoxy)stannanes by use of Hypercoordinated Sn Monomers

Pau

D’Amaral

Lough

et al. 2018

Chemistry A European J

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“…For more than 20 years, dialkyl and diaryl homopolystannanes have been prepared by reductive coupling of either tindichlorides 7,8,[12][13][14][15][16][17] or tindihydrides. 5,6,9,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] These intriguing polymers possess a backbone of σ-σ delocalized 6,7,8,12,[15][16][17][18][19][20][21][22][23][24]26,24 organotins envisioned for use as processable intrinsic semiconductors [12][13][14][15]18,24,26,…”

Section: 2-introductionmentioning

confidence: 99%

“…5,6,9,[18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] These intriguing polymers possess a backbone of σ-σ delocalized 6,7,8,12,[15][16][17][18][19][20][21][22][23][24]26,24 organotins envisioned for use as processable intrinsic semiconductors [12][13][14][15]18,24,26,33 or printable polymeric wires. [13][14][15][16][17]23 Along with the considerable synthetic challenges in preparing later Group 14 polymeric materials is their profound sensitivity to moisture and light 5,…”

Section: 2-introductionmentioning

confidence: 99%

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Alternating polystannanes: synthesis, preparation, characterization and a computational study

Harrypersad¹

2021

Preprint

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Polystannanes have been synthesized by a number of useful routes. Generally, these polymers have been limited to homopolymers containing a single type of substituent. We now demonstrated a novel condensation polymerization utilizing dialkyl or diaryl tin dihydrides and dialkyl tin diamides to prepare alternating polymers with neighbouring tin centers possessing different group functionalities. Three new alternating polystannanes containing both organically solubilizing (n-Bu, Me) and less solubilizing (Ph) side groups as well as the homopolymer dibutylpolystannane have been prepared. A variety of closely related model tristannanes using the same synthetic methodology was also completed. We have also carried out a computational study of a number of model stannanes in order to optimize structures of the oligo- and polystannanes synthetically prepared and predict their spectral properties by using time dependent density functional theory (TD-DFT). This study has yielded results that can be influential in predicting chemical orientation, bonding properties and electronics.

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Catenated Germanium and Tin Oligomers and Polymers

Foucher

2017

Main Group Strategies Towards Functional Hybrid Materials

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Reaction products of dichlorodiorganostannanes with sodium in liquid ammonia: In-situ investigations with 119Sn NMR spectroscopy and usage as intermediates for the synthesis of tetraorganostannanes

Cited by 12 publications

References 51 publications

Synthesis and Characterization of Readily Modified Poly(aryl)(alkoxy)stannanes by use of Hypercoordinated Sn Monomers

Synthesis and Characterization of Readily Modified Poly(aryl)(alkoxy)stannanes by use of Hypercoordinated Sn Monomers

Alternating polystannanes: synthesis, preparation, characterization and a computational study

Catenated Germanium and Tin Oligomers and Polymers

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