2,3,6,7,10,11-Hexakis(hexyloxy)triphenylene - HAT6

CAS Number 70351-86-9

Electron / Hole Transport Layer Materials, Liquid Crystals, Materials, Optoelectronic Materials, Perovskite Interface Materials, Perovskite Materials, Semiconducting Molecules

MSDS

2,3,6,7,10,11-Hexakis(hexyloxy)triphenylene - HAT6 CAS 70351-86-9

Discotic Liquid Crystals (DLCs) with Triphenylenes

A model molecule for DLC studies and a hole transport layer for perovskite solar cells

Specifications | MSDS | Literature and Reviews

2,3,6,7,10,11-Hexakis(hexyloxy)triphenylene, also known as HAT6 (CAS number 70351-86-9), has a hexagonal fused triphenylene core structure. Six n-hexyloxy side chains are symmetrically distributed onto the triphenylene core at 2,3,6,7,10,11-positions. The six side chains are there to promote solubility in organic solvents and enhance electron density of the triphenylene core. Study showed that the dynamics of the cores and tails of discotic molecules are strongly correlated. HAT6 has been referred to as the model molecule for the study of the DLCs.

At room temperature, HAT6 is a plastic crystal where the cores are tilted with respect to the columnar axes. Two phase transition temperatures at about 65 °C and 100 °C are observed in the differential scanning calorimetry study of HAT6. This corresponds to the melting of the columnar hexagonal (Col_H) and plastic crystalline phases into the isotropic and Col_H phases, respectively.

HAT6 DLC has also been employed as a transparent hole transport material for perovskite solar cells to promote ambient and thermal stability. These perovskite solar cell devices retained 93% of the initial efficiency for 690 h and 92% after 1200 h under ambient conditions.

General Information

CAS Number	70351-86-9
Chemical Formula	C₅₄H₈₄O₆
Molecular Weight	829.24 g/mol
Absorption*	λ_max 278 nm (in DCM)
Fluorescence	n.a.
HOMO/LUMO	HOMO = 5.23 eV, LUMO = 1.88 eV (E_g = 3.35) [1]
Synonyms	H6TP, HHOTP, HAT6
Classification or Family	Triphenylene, Discotic liquid crystals, Hole transport layer materials.

Product Details

Purity	>98% (HPLC)
Melting Point	DSC: T_g = 65 °C, 100 °C
Appearance	Off-white to pale yellow powder/crystal

* Sublimation is a technique used to obtain ultra pure-grade chemicals, see sublimed materials for OLED devices.

Chemical Structure

MSDS Documentation

HAT6 - 2,3,6,7,10,11-Hexakis(hexyloxy)triphenylene MSDS Sheet

Literature and Reviews

Synthesis and investigation on liquid crystal and optical properties of dyads based on triphenylene and perylene, X. Kong et al., RSC Adv., 7, 17030 (2017); DOI: 10.1039/c7ra01320e.
Dynamics of a Triphenylene Discotic Molecule, HAT6, in the Columnar and Isotropic Liquid Phases, F. Mulder et al., J. Am. Chem. Soc., 125 (13), 3860–3866 (2003); DOI: 10.1021/ja029227f.
Molecular ordering of the discotic liquid crystal HAT6 confined in mesoporous solids, S. Całus et al., Microporous Mesoporous Mater., 197, 26-32 (2014); DOi: 10.1016/j.micromeso.2014.05.036.

Transparent Liquid Crystal Hole-Transporting Material for Stable Perovskite Solar Cells, A. Ain et al., Sol. RRL, 7 (2), 2200920 (2023); DOI: 10.1002/solr.202200920.
Conformation, Defects, and Dynamics of a Discotic Liquid Crystal and Their Influence on Charge Transport, L. Haverkate et al., J. Phys. Chem. B, 115 (47), 13809–13816 (2011); DOI: 10.1021/jp2068478.
Crystalline solid retains memory of anisotropy in precursor liquid crystalline phase, K. Bagchi et al., J. Mater. Chem. C, 11, 11466-11475 (2023); DOI: 10.1039/D3TC01175E.
Polymeric ultralong organic phosphorescence with excellent humidity and temperature resistance via hydrophobic effect, Z. Li et al., Aggregate, e440 (2023); DOI: 10.1002/agt2.440.
Recent Advances and Prospects of Small Molecular Organic Thermoelectric Materials, D. Zhou et al., Small, 18 (23), 2200679 (2022); DOI: 10.1002/smll.202200679.