1345614-94-9

Basic information

• Product Name: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole
• Synonyms: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole
• CAS NO: 1345614-94-9
• Molecular Formula: C25H26BNO2
• Molecular Weight: 383.29044
• Mol File: 1345614-94-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 166 °C
• Boiling Point: 489.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole(1345614-94-9)
• EPA Substance Registry System: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole(1345614-94-9)

Safety Data

• Hazardous Substances Data: 1345614-94-9(Hazardous Substances Data)

Usage

Chemical compound

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-9H-carbazole

Molecular structure

Contains a carbazole core with a boron-containing group and a p-tolyl substituent

Boron-containing group

4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, a boronic ester used in organic synthesis and as a building block for various functional materials

p-tolyl substituent

A common aromatic group that imparts certain properties to the compound

Potential applications

Organic electronics, optoelectronic devices, materials science.

Upstream product

• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 86-74-8 9H-carbazole 
• 731016-44-7 3,6-bromo-9-(p-tolyl)-1,2,3,4,4a,9a-hexahydrocarbazole 
• 73183-34-3 bis(pinacol)diborane 
• 19264-73-4 9-(4-methylphenyl)-9H-carbazole 

Relevant articles and documents

9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole—A new donor building-block in the design of sensitizers for dye-sensitized solar cells

The novel donor building-block - 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole was designed and employed in the synthesis of dye-sensitized solar cell (DSSCs). An effective, high-yielding synthesis of 4,6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9-(p-tolyl)-1,2,3,4,4a,9a-hexahydrocarbazole from 1,2,3,4,4a,9a-hexahydrocarbazole was realized. Three new metal-free organic sensitizers, containing the new donor building block were prepared by a stepwise approach from 4,7-dibromobenzo[c][1,2,5]chacogenadiazoles. A 2,1,3-Benzothiadiazole dye containing hexahydrocarbazole donor, thiophene as π-spacer and cyanoacrylate as anchoring electron acceptor showed photovoltaic properties higher than the well-known WS-2 sensitizer with PCE = 5.86 %. Although benzoxa- and –selenadiazole dyes have a bathochromic shift (24?30 nm) in the UV–vis spectra, and smaller energy gap Eg (about 0.1 eV), they have lower photovoltaic parameters, including PCE of 1.5–2.3 %. Introducing a new donor 9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole into the construction of the DSSCs has broadened possibilities for the optimization of their photovoltaic properties.

Bipolar hosts for light emitting devices

Some embodiments provide a compound represented by Formula 1: wherein R1, R2, R3, R4, R5, R6, R7 and R8 are independently H, C1-C3 alkyl, or C1-3 perfluoroalkyl; HT is optionally substituted carbazoyl, optionally substituted phenylcarbazolyl, optionally substituted (phenylcarbazolyl)phenyl, optionally substituted phenylnaphthylamine, or optionally substituted diphenylamine; and ET optionally substituted benzimidazol-2-yl, optionally substituted benzothiazol-2-yl, optionally substituted benzoxazol-2-yl, optionally substituted 3,3′-bipyridin-5-yl, optionally substituted quinolin-8-yl, optionally substituted quinolin-5-yl, or optionally substituted quinoxalin-5-yl. Other embodiments provide an organic light-emitting diode device comprising a compound of Formula 1.