Skip to Content
Merck

Key Documents

View All Documentation

922285

TpOx-Ph-o-Cl

Synonym(s):

TpOx-Aryl-Hal Series

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C50H64ClNO6
CAS Number:
2377209-52-2
Molecular Weight:
810.50
MDL number:
MFCD00048045
NACRES:
NA.23
UNSPSC Code:
12352200
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

100

description

Emissive Layer, Polymorph crystalline phase: Solid, Discotic Liquid Crystal, Isotropic

transition temp

discotic phase to isotropic phase 148 °C (heating), crystalline phase to discotic phase 89 °C (heating)

solubility

soluble (THF > 1 mg/mL, MeCN < 0.63 mg/mL, DMSO < 0.43 mg/mL, DCM > 1 mg/mL)

λmax

271 nm in ethyl acetate

εmax

61,000 M-1cm-1 in ethyl acetate

fluorescence

λem 499 nm, quantum yield 0.53 (pSS(nm) = 228; Fluorescence lifetime (ns) = 6.49)

storage temp.

−20°C

General description

TpOx-Ph-o-Cl is a UV excitable fluorescent material with a polycyclic aromatic donor-acceptor structure where the triphenoxazole core acts as a donor and the aromatic group on the two position of the oxazole (2-chloro-phenyl) act as the acceptor group. The push-pull, donor-acceptor, structure facilitates intramolecular charge transfer in the excited state that results in a 228 nm emission Stokes Shift. TpOx-Ph-o-Cl is also a photo-conducting Discotic Liquid Crystalline (DLC) material with mesophase transition onset temperature of 89°C. TpOx-Ph-o-Cl is designed for 355 nm and 405 nm excitation with emission at 499 nm with quantum yield of 0.53, high thermal, chemical and photostability. TpOx-Ph-o-Cl has potential uses in fluorescent dye staining, organic electronic and photonics, and imaging applications.

Application

Fluorescent materials have a range of unique properties that allows for potential use in a range of applications:
  • Fluorescent dye staining
UV fluorescent materials can be used to dope polymer and resin composites, including 3D applications, and further identified using fluorescence emission.
  • Organic semiconductor for organic electronic and photonic applications
These organic discotic liquid crystals display columnar hexagonal mesophase, and were incorporated into OPV device as a hole transport layer and donor material. Similar compounds have been used in organic light emitting devices (OLEDs), organic photovoltaic device (OPVs) and organic field-effect transistor (OFETs) as hole transport material.
  • Multi-photon microscopy
These UV fluorescent materials have been used in multi-photon microscopy, showing remarkable image resolution relative to commercial fluorophores in the multiphoton microscopy imaging. By perfusing it into an ex-planted human liver, it was possible to observe fluorophore staining of the hepatocytes and T-cells in the liver vasculature. During the live liver imaging these probes have been shown to perfuse effectively in human tissue and emit brightly without significant cytotoxicity during the course of the experiment.

Disclaimer

Storage: Store under nitrogen in the dark in the freezer (below 8 Celsius).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCX0583

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

Triphenoxazoles: Fluorescent Photoconducting Materials

Triphenoxazoles exhibit tunable properties, liquid crystallinity, and potential for modification.