Synthesis of Siloles (and Germoles) that Exhibit the AIE Effect

Corey, Joyce Y.

doi:10.1002/9781118735183.ch01

Cited by 3 publications

(7 citation statements)

References 180 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction proceeded by elimination of Me 3 SiCl, and new Si-N and B-N bonds were formed to give the spirosilane 8a in high purity (Ͼ99 %). The structure of 8a in solution follows from the NMR spectroscopic data ( 1 H, 13 C, 15 N, 11 B, and 29 Si) and was confirmed by single-crystal X-ray diffraction (see below).…”

Section: A New Spirosilanementioning

confidence: 92%

“…The latter is shown by the splitting of the relevant 1 H and 13 C NMR signals (shown for some examples in Figure 2). Other convincing arguments for the structural assignments such as the 11 B, 13 C, and 29 Si chemical shifts and spin-spin coupling constants, in particular n J29 Si, 13 C , have been discussed previously for related derivatives. [21] As the X-ray diffraction studies indicated negligible intermolecular interactions, the comparison between calculated gas-phase structures and direct structural evidence from the solid state is meaningful.…”

Section: Nmr Spectroscopy and Dft Calculationsmentioning

confidence: 94%

“…Table 1. 13 C, 11 B, and 29 Si NMR spectroscopic data [a] of spirosilane derivatives 3-5. Table 2 for selected bond lengths and angles.…”

Section: 2-hydoboration and 11-carboborationmentioning

confidence: 99%

“…The remaining Si-C function in (CH 2 =CH) 2 Si(Cl)CϵCtBu opens the way to new spirosilanes after a sequence of hydroboration/carboboration/hydroboration, for which a first example was studied. The products were characterized by X-ray diffraction in the solid state and NMR spectroscopy in solution ( 1 H, 11 B, 13 C, 15 N, 29 Si), complemented by optimization of gas-phase structures and calculation of NMR parameters by DFT methods. tions appears to be versatile in synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] With silicon, heterocycles such as 1-silacyclobutenes, [4][5][6] 1-silacyclopent-2-enes, [7,8] 1-silacyclohex-2-enes, [7,9] and silole derivatives are particularly noteworthy. [10][11][12] Addressing 1-silacyclopent-2-enes, numerous derivatives bearing functionalities such as Si-organyl, Si-Cl, and Si-H at a chiral silicon atom have become available (Figure 1, example A). The processes of 1,2-hydroboration [13] and 1,1-carboboration [14] are simple, efficient, and cost effective.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Synthesis and Characterization of Spirosilanes – 1,2‐Hydroboration and 1,1‐Carboboration

et al. 2014

View full text Add to dashboard Cite

Starting from dichloro(divinyl)silane, the dialkynyl(divinyl)-silanes (CH 2 =CH) 2 Si(CϵCR) 2 (R = tBu, p-tolyl, 3-thienyl, CH 2 NMe 2 ) were prepared. These silanes were treated with 9-borabicyclo[3.3.1]nonane (9-BBN) for 1,2-hydroboration of the vinyl groups. The hydroboration products rearranged quickly and quantitatively by intramolecular 1,1-carboboration into the respective target compounds, the axially chiral 5-silaspiro[4.4]nona-1,6-dienes bearing boryl groups at the 2-and 7-positions and the R substituents at the 1-and 6-posi-

show abstract

Section: A New Spirosilanementioning

confidence: 92%

Section: Nmr Spectroscopy and Dft Calculationsmentioning

confidence: 94%

“…Table 1. 13 C, 11 B, and 29 Si NMR spectroscopic data [a] of spirosilane derivatives 3-5. Table 2 for selected bond lengths and angles.…”

Section: 2-hydoboration and 11-carboborationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and Characterization of Spirosilanes – 1,2‐Hydroboration and 1,1‐Carboboration

et al. 2014

View full text Add to dashboard Cite

show abstract

Synthesis and characterization of luminescent 2,7-disubstituted silafluorenes

Hammerstroem

Braddock‐Wilking

Rath

2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

The synthesis and characterization of a series of six new highly fluorescent 2,7alkynyl(aryl)-3,6-dimethoxy-9,9-diphenylsilafluorenes was investigated utilizing a modified multi-step synthetic pathway in which the final step utilizes palladium-catalyzed cross-coupling conditions to incorporate a variety of conjugatedalkynyl(aryl) groups at the 2,7-positions. These new compounds were characterized utilizing X-ray crystallography as well as multinuclear NMR, EA, TGA, DSC, UV-Vis, and fluorescence spectroscopic techniques. The new silafluorene compounds show a strong absorption band in the visible region with a maximum in the region of 374-388 nm and an emission maximum in the range of 403-420 nm. The solution-state quantum efficiencies for the luminescence are high and range from 0.80-0.89. All of the compounds show high thermal stability as determined by DSC and TGA analysis. Conjugated π-electron systems containing silicon have received substantial attention for their use as components for a wide variety of optical and electronic applications such as organic light emitting diodes (OLEDs), photovoltaic devices, field-effect transistors (FETs), and as chemical and biological sensors. 1-18 The unique optoelectronic properties found in these silicon systems arises from the σ*−π* conjugation between the σ* orbital of the two exocyclic groups at the silicon center and π* orbital of the butadiene unit of the ring resulting in a low energy LUMO level. 16,17 Incorporation of conjugated organic moieties on the ring allows for further electronic tuning. 1-22 Silafluorenes represent a relatively new class of photoluminescent molecules which demonstrate smaller band gaps, deep blue emission, high electron affinity, improved thermal stability, and greater quantum yields than that of their fluorene and carbazole analogs. 15,23-30 Silafluorenes are analogs of 9,9-dialkylfluorenes, which have been of interest due to their deep blue emission and their ability to be incorporated into polysilafluorenes. 11,24,26,27,30-37 Commercially available blue emitting polyfluorenes generally have a much shorter lifetime compared to that of red and green emitters. As a result, there has been increased interest in strong blue emitters with high quantum efficiency, lifetime, and color purity. Unfortunately, some polyfluorenes can undergo a decrease in emission and spectral broadening resulting in a low-energy green band over time. 38-40

show abstract