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695572

Sigma-Aldrich

m-Carborane-1-thiol

96%

Synonym(s):

1,7-Dicarba-closo-dodecaborane-1-yl-thiol, 1,7-Dicarbadodecaborane(12)-1-thiol, 1-Mercapto-m-carborane

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About This Item

Empirical Formula (Hill Notation):
C2H12B10S
CAS Number:
56310-80-6
Molecular Weight:
176.29
MDL number:
MFCD01746118
UNSPSC Code:
12352103
PubChem Substance ID:
329761752

assay

96%

form

solid

mp

195-209 °C

SMILES string

SC12BBBBBBBBBC1B2

InChI

1S/C2H12B10S/c13-2-1(3-2)4-6-8-10-12-11-9-7-5-2/h1,3-13H

InChI key

IKKUVNFZJOSSLF-UHFFFAOYSA-N

General description

m-Carborane-1-thiol (M1) is a boron cluster compound that is also known as icosahedral carborane thiol. It forms a self-assembled monolayer (SAM) by attaching the thiol groups with surface atoms. This SAM forms a two dimensional matrix on the metal surface that enables the tuning of surface properties such as a work function, and wettability.[1][2][3]

Application

M1 forms a mixed SAM with m-carborane-9-thiol (M9), which is used to tune the work function of gold and silver surfaces for the fabrication of organic light emitting diodes (OLEDs).[4][5]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ4414
SHBG3980V
07926MH

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?Carboranyl-cysteine??Synthesis, Structure and Self-Assembly Behavior of a Novel alpha-Amino Acid.
He T, et al.
Scientific Reports, 7(1), 16995-16995 (2017)
A coordination chemistry dichotomy for icosahedral carborane-based ligands.
Spokoyny AM, et al.
Nature Chemistry, 3(8), 590-590 (2011)
Mixed carboranethiol self-assembled monolayers on gold surfaces.
Yavuz A, et al.
Applied Surface Science, 413(1), 233-241 (2017)
Synthesis and properties of substituted icosahedral carborane thiols.
Plesek J and Stanislav H
Collection of Czechoslovak Chemical Communications, 46(3), 687-692 (1981)
Benjamin Foerster et al.
Science advances, 5(3), eaav0704-eaav0704 (2019-03-28)
The chemical nature of surface adsorbates affects the localized surface plasmon resonance of metal nanoparticles. However, classical electromagnetic simulations are blind to this effect, whereas experiments are typically plagued by ensemble averaging that also includes size and shape variations. In
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