958293-23-7

Basic information

• Product Name: 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene
• Synonyms: 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene;9,9-Dioctyl-9H-9-silafluorene-2,7-bis(boronic acid pinacol ester);5,5-Dioctyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-dibenzo[b,d]silole;9H-9-Silafluorene, 9,9-dioctyl-2,7-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-5,5-dioctyl-dibenzo[b,d]silole;5,5-Dioctyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-5,5-Dioctyl-3,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H- dibenzo[b,d]silole;2-[5,5-dioctyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b][1]benzosilol-7-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 958293-23-7
• Molecular Formula: C₄₀H₆₄B₂O₄Si
• Molecular Weight: 658.64
• Product Categories: Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Materials Science;New Products for Materials Research and Engineering;Organic and Printed Electronics
• Mol File: 958293-23-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 115-120℃
• Boiling Point: 682.2 °C at 760 mmHg
• Flash Point: 366.4 °C
• Appearance: /
• Density: 1.01
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene(958293-23-7)
• EPA Substance Registry System: 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene(958293-23-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 958293-23-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 958293-23-7 differently. You can refer to the following data:
1. 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-9-silafluorene is used in the synthesis of low-band gap photovoltaic polymer materials that give power conversion efficiences of approx 3%1.
2. This material is used in the synthesis of low-band gap photovoltaic polymer materials that give power conversion efficiences of approx 3%.

Upstream product

• 891182-24-4 3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 852138-89-7 4,4’-dibromo-2,2’-diiodo-1,1’-biphenyl 
• 18416-07-4 dichloro(dioctyl)silane 
• 136630-36-9 4,4′-dibromo-[1,1′-biphenyl]-2,2′-diamine 
• 91371-12-9 4,4'-dibromo-2,2'-dinitrobiphenyl 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 73183-34-3 bis(pinacol)diborane 

Relevant articles and documents

Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application

The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.

The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics. To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials by the respective combination of either a 3,6- or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-linked-N- octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised using 1H, 13C{1H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration: glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence. The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 × 10-4 cm2 V-1 s-1 and on/off current ratios of 105. The Royal Society of Chemistry 2011.

Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory

Realizing p-channel semiconducting polymers with good hole mobility, solution processibility, and air stability is an important step forward in the chemical manipulation of charge transport in polymeric solids and in the development of low-cost printed electronics. We report here the synthesis and full characterization of the dithienosilole- and dibenzosilole-based homopolymers, poly(4,4-di-n-hexyldithienosilole) (TS6) and poly(9,9-di-n- octyldibenzosilole) (BS8), and their mono- and bithiophene copolymers, poly(4,4-di-n-hexyldithienosilole-alt-(bi)thiophene) (TS6T1, TS6T2) and poly(9,9-di-n-octyldibenzosilole-alt-(bi)thiophene) (BS8T1,BS8T2), and examine in detail the consequences of introducing dithienosilole and dibenzosilole cores into a thiophene polymer backbone. We demonstrate air-stable thin-film transistors (TFTs) fabricated under ambient conditions having hole mobilities as large as 0.08 cm2/V·s, low turn-on voltages, and current on/off ratios > 106. Additionally, unencapsulated TFTs fabricated under ambient conditions are air-stable, an important advance over regioregular poly(3-hexylthiophene) (P3HT)-based devices. Density functional theory calculations provide detailed insight into the polymer physicochemical and charge transport characteristics. A direct correlation between the hole injection barrier and both TFT turn-on voltage and TFT polymer hole mobility is identified and discussed, in combination with thin-film morphological characteristics, to explain the observed OTFT performance trends.