Multi-maleimides bearing electron-donating chromophores: reversible fluorescence and aggregation behavior.

A((=))-D, [A((=))](2)-D and [A ((=))](3)-D multi-maleimides and multi-itaconimides bearing electron-donating chromophores display a strong fluorescence quenching due to an intramolecular charge-transfer interaction. The electron-accepting C=C bond plays a key role in the intramolecular quenching. For the isomerization of these multi-itaconimides and Michael additions of these multi-maleimides, their emission behavior is irreversible. For the Diels-Alder additions of these multi-maleimides, their emission behavior is reversible due to the reversible opening and closing of intramolecular charge-transfer pathway. Tris-maleimide TMPA peripherally modified with furfural alcohol displays not only reversible fluorescence behavior but also reversible aggregation behavior.