922811

TpOx-2-Nap

• Synonym(s): 8-(Naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole
• Empirical Formula (Hill Notation): C₅₄H₆₇NO₆
• CAS Number: 2377209-28-2
• Molecular Weight: 826.11
• NACRES: NA.23

Properties

• band gap: 3.57 eV, Optical, Solution state
• Quality Level: 100
• solubility: soluble (THF > 1 mg /mL, MeCN < 0.33 mg / mL, DMSO < 0.03 mg / mL, DCM > 1 mg /mL)
• λmax: 164,000 M^-1cm^-1 at 272 nm in ethyl acetate
• fluorescence: λ_em 494 nm, quantum yield 0.55 (pSS (nm) = 222, Fluorescence Lifetime (ns) = 5.45)
• orbital energy: HOMO -5.45 eV (CV); LUMO -2.47 eV (CV)
• storage temp.: −20°C

Description

General description

• Thermal degradation onset = ∼380 °C
• Polymorph crystalline phase: Solid, Discotic Liquid Crystal, Isotropic
• Phase transition temperature:
• Heating: Crys - Colh – 96 °C, Colh - Iso – 168 °C
• Cooling: Iso - Colh – 161 °C, Colh - Crys – 43 °C

TpOx-2-Nap 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-naphthalene) act as the acceptor group. The push-pull, donor-acceptor, structure facilitates intramolecular charge transfer in the excited state that results in a 222 nm emission Stokes Shift. This oxazole is also a photo-conducting Discotic Liquid Crystalline (DLC) material with mesophase transition onset temperature of 96 °C. It is designed for 355 nm and 405 nm excitation with emission at 494 nm with quantum yield of 0.55, 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)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable