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Fluorescent benzo[a]phenoxazinium chlorides possessing undecylamino chains with functionalised ending-groups (hydroxyl, carboxylic acid and the ester group) as substituents at the 5-position of the heterocycles were successfully synthesised and characterised. These compounds were used in photophysical studies with DNA, and compared to the corresponding analogue with a non-functionalised terminal (methyl group). It was found that the functionalised terminal exerts a dramatic influence on the type of interaction with the hydroxyl group promoting intercalation, while the ester group promotes groove binding.

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Five benzo [a]phenoxazinium chlorides containing alkyl chains with twenty carbon atoms at the 5-or 9-positions of the tetracyclic ring were efficiently synthesised and characterised by UV/Vis and NIR spectroscopy. The absorption and emission maxima in ethanol occur in the range 627-641 nm and 645-676 nm, respectively, with quantum yields varying from 0.14 to 0.38. Preliminary photophysical studies with these fluorochromophores in zwitterionic [2,3-bis(palmitoyl-

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