Excited-State Intramolecular Proton Transfer in Schiff Bases
Summary
Schiff bases are imine compounds, typically formed by the condensation of primary amines with aldehydes or ketones, which often feature an adjacent hydroxyl group capable of forming a strong intramolecular hydrogen bond. Upon photoexcitation, many of these systems undergo excited-state intramolecular proton transfer (ESIPT), in which a proton shifts across the hydrogen bond to generate a tautomeric species in the excited state. This process yields large Stokes shifts, dual emission bands and ultrafast photodynamics that are highly sensitive to local environment, molecular conformation and electronic structure. ESIPT in Schiff bases underpins diverse applications—from fluorescent probes and molecular photoswitches to dye-sensitised solar cells and optoelectronic devices—by enabling tunable emission wavelengths, enhanced photostability and rapid response to external stimuli. Recent advances have focussed on rational ligand design, substituent effects and theoretical modelling to control proton-transfer pathways and optimise performance in sensing, imaging and energy-conversion contexts.
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Excited-State Intramolecular Proton Transfer in Schiff Bases publication trend
The graph below shows the total number of articles in excited-state intramolecular proton transfer in schiff bases across all publications each year (not limited to Nature Index journals).
Technical terms
Schiff base: A compound containing a carbon–nitrogen double bond formed by condensation of an amine with a carbonyl group.
Excited-State Intramolecular Proton Transfer (ESIPT): A process in which a proton relocates within a molecule from a donor to an acceptor site through a hydrogen bond after electronic excitation.
Tautomerism: The reversible interconversion between structural isomers (tautomers) that differ in the position of a proton and a double bond.
Intramolecular hydrogen bond: A hydrogen bond formed between donor and acceptor groups within the same molecule, stabilising specific conformations and enabling proton transfer.
Quantum yield: The ratio of the number of molecules undergoing a specified photophysical or photochemical event to the number of photons absorbed.
References
- New pyrene and fluorene-based π-conjugated Schiff bases: Theoretical and experimental investigation of optical properties. Journal of the Serbian Chemical Society (2024).
- UV-Induced Benzyloxy Rotamerization in an Ortho OH-Substituted Aryl Schiff Base. Photochem (2022).
- Solvent Influence on Absorption Spectra and Tautomeric Equilibria of Symmetric Azomethine‐Functionalized Derivatives: Structural Elucidation and Computational Studies. ChemistryOpen (2022).
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