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922854

Sigma-Aldrich

TpOx-Ph-m-CF3

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Synonym(s):
2,3,6,11,12-Pentakis(pentyloxy)-8-(3-(trifluoromethyl)phenyl)triphenyleno[1,2-d]oxazole
Empirical Formula (Hill Notation):
C51H64F3NO6
CAS Number:
2612025-76-8
Molecular Weight:
844.05
NACRES:
NA.23

description

Polymorph crystalline phase: Solid, Discotic Liquid Crystal, Isotropic

Quality Level

100

band gap

2.94 eV (Optical, Solution state)

transition temp

crystalline phase to discotic phase 132 °C (heating)
discotic phase to isotropic phase 243 °C (heating)

solubility

soluble (THF > 1 mg /mL, MeCN < 0.4 mg/mL, DMSO < 0.27 mg/mL, DCM > 1 mg/mL)

λmax

271 nm in ethyl acetate

εmax

73,000 M-1cm-1 in ethyl acetate

fluorescence

λem 503 nm, quantum yield 0.48 (pSS(nm) = 232; Fluorescence lifetime (ns) = 7.07)

Orbital energy

HOMO -5.47 eV (CV)
LUMO -2.52 eV (CV)

storage temp.

−20°C

Related Categories

General description

TpOx-Ph-m-CF3 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 (3-trifluoromethyl-phenyl) act as the acceptor group. The push-pull, donor-acceptor, structure facilitates intramolecular charge transfer in the excited state that results in a 232 nm emission Stokes Shift. This oxazole is also a photo-conducting Discotic Liquid Crystalline (DLC) material with mesophase transition onset temperature of 132 °C. It is designed for 355 nm and 405 nm excitation with emission at 503 nm with quantum yield of 0.48, high thermal, chemical and photostability. This luminescent compound 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.

Storage and Stability

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Triphenoxazoles: Fluorescent Photoconducting Materials

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

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