A modified route to unsymmetrically substituted triphenylenes, new functionalised derivatives and twins, and the smallest reported triphenylene mesogen

ABSTRACT

We report the unexpected observation of columnar mesophase formation in a simple 2,7-dibromotetramethoxytriphenylene – by far the most lightly substituted discotic mesogen in this class. This derivative was prepared alongside the 3,6-dibromotriphenylene isomer to demonstrate an alternative, modified synthetic strategy that permits late-stage interchange of alkyl chain substituents. The new method is employed alongside the original route to deliver several new materials, including a conjugated ferrocene–triphenylene–ferrocene triad, a BODIPY–triphenylene–BODIPY triad and a new nematic twin linked through imine bridges.

Graphical Abstract

KEYWORDS:

• John Goodby
• triphenylenes
• discotics
• synthesis
• functionalisation

Acknowledgements

We thank INTERREG IVA (IS:CE 4061 and AI Chem Channel 4196), the Cultural Bureaux of Saudi Arabia and TETFUND Nigeria for financial support, and the EPSRC Mass Spectrometry Service (Swansea).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

We thank INTERREG IVA (IS:CE 4061 and AI Chem Channel 4196), the Cultural Bureaux of Saudi Arabia and TETFUND Nigeria for financial support, and the EPSRC Mass Spectrometry Service (Swansea).