Synthesis of Aryl‐Substituted Hexa‐Alkynyl Hexaazatrinaphthylenes via Sonogashira Coupling and Evaluation of Their Photophysical Properties

TL;DR

Researchers synthesized new HATNA derivatives using Sonogashira coupling and found they have strong light-absorbing and efficient light-emitting properties.

Contribution

A new synthesis method for hexa(arylethynyl) HATNA derivatives with good yields and favorable photophysical properties.

Findings

The synthesis protocol showed good functional-group tolerance and moderate to good yields.

The HATNA derivatives exhibited high molar absorption coefficients up to 1.69 × 10⁵ M⁻¹ cm⁻¹.

Quantum yields of up to 0.73 were observed, indicating strong photophysical performance.

Abstract

Hexaazatrinaphthylene (HATNA) has recently been a subject of great interest as a polycyclic heteroaromatic scaffold in materials science, specifically in the field of discotic liquid crystals (DLCs), battery cathodes, n‐type semiconductors, and so on. However, little is known about the photophysical properties of HATNA derivatives. Here we report the synthesis of a new class of hexa(arylethynyl) HATNA derivatives via consecutive Sonogashira coupling. This protocol showed good functional‐group tolerance and moderate to good yields were achieved. The obtained HATNA products showed favorable photophysical properties, with molar absorption coefficients up to 1.69 × 105 (M−1 cm−1) and high quantum yields up to 0.73.

A new series of hexaalkynyl‐substituted hexaazatrinaphthylene (HATNA) derivatives was successfully synthesized via Sonogashira coupling between hexabromo‐HATNA and aryl‐substituted terminal alkynes. This protocol exhibited good functional‐group tolerance, affording the desired products in moderate to good yields. The resulting HATNA derivatives were confirmed to possess favorable photophysical properties, including high molar absorption coefficients and quantum yields of up to 0.73.

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