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277592

Sigma-Aldrich

9-Vinylcarbazole

98%

Synonym(s):

9-Vinyl-9H-carbazole, N-Ethenylcarbazole, N-Vinylcarbazole

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About This Item

Empirical Formula (Hill Notation):
C14H11N
CAS Number:
Molecular Weight:
193.24
Beilstein:
132988
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Assay

98%

bp

154-155 °C/3 mmHg (lit.)

mp

60-65 °C (lit.)

SMILES string

C=Cn1c2ccccc2c3ccccc13

InChI

1S/C14H11N/c1-2-15-13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h2-10H,1H2

InChI key

KKFHAJHLJHVUDM-UHFFFAOYSA-N

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General description

9-Vinylcarbazole (9-VC) is a monomer characterized by photochemical properties, thermal stability, and high reactivity due to its vinyl group. It enhances the performance of conducting polymers and thermosetting resins. In drug delivery systems, 9-VC facilitates the encapsulation of therapeutic agents, enabling controlled release and improved efficacy, particularly in cancer therapy. Additionally, its photochemical capabilities allow for advancements in photonic devices.

Application

9-Vinylcarbazole can be used:
  • As a monomer to synthesize electrochromic conductive thin film copolymer with 3,4-ethylenedioxythiophene (EDOT), for smart windows and flexible electronic displays.
  • As a precursor to prepare a copolymer which is used to fabricate highly efficient polymeric thermally activated delayed fluorescent (TADF) organic light-emitting diode (OLED) with high quantum efficiency.
  • As a functional monomer to synthesize poly(vinyl carbazole) (p(VC)) microgel particles via surfactant free emulsion polymerization. These microgels find application in the field of drug delivery and tissue engineering.
  • As a precursor to fabricate hole transport layer for perovskite solar cells.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Muta. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Merve Kara et al.
Macromolecular rapid communications, 36(23), 2070-2075 (2015-09-12)
A new phenacyl-type photoinitiator based on ethyl carbazole as a long wavelength photo-initiator is developed for free radical polymerization. Phenacyl ethyl carbazolium hexafluoroantimonate (PECH) photoinitiator is synthesized in a two-step, one-pot manner by quaternizing ethyl carbazole with phenacyl bromide and
Ceren Kütahya et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(46), 10444-10451 (2020-04-29)
NIR exposure at 790 nm activated photopolymerization of monomers comprising UV-absorbing moieties by using [CuII /(TPMA)]Br2 (TPMA=tris(2-pyridylmethyl)amine) in the ppm range and an alkyl bromide as initiator. Some of them comprised structural elements selected either from those showing proton transfer or

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