Theoretical insights into the linker effects on the turn-on fluorescence behaviors in pyridazinone-containing NO probes

[Display omitted] •Three pyridazinone‑containing dyes have been theoretically designed.•PYSSNO and PYSONO are promising candidates for novel NO probes.•PYONO is not suitable as a NO probe. Fluorescent probes with preferred photophysical properties have attracted considerable attention for their advantages in real-time and accurate detection of signalling molecules in living organisms. Nitric oxide (NO) is a ubiquitous cellular messenger closely associated with many physiological and pathological processes. A NO fluorescent probe, PYSNO, based on the pyridazinone (PY) scaffold with o-phenylenediamine as the receptor and thiophene (S) as the linker has been synthesized. Inspired by the experimental guidance, three other dyes (PYSSNO, PYSONO and PYONO) were theoretically designed by replacing the S linker with thieno[3,2-b]thiophene (SS), thieno[3,2-b]thiophene 1,1-dioxide (SO) and thiophene 1,1-dioxide (O) groups. The photophysical properties were theoretically investigated in aqueous solution, by the combined time-dependent density functional theory, polarizable continuum model and thermal vibration correlation function approaches. Our results indicate that the emission wavelengths of all the designed dyes show red shifts due to either an increase in the conjugation length or electron-accepting ability of the linkers compared to PYSNO. The photoinduced electron transfer (PET) processes are all absent in these systems. PYSSNO and PYSONO are theoretically expected to be promising candidates for novel NO fluorescent probes, but the suitability of PYONO as a NO probe is compromised by the predicted non-luminescent emission before and after reaction with NO. Our study not only offers valuable insights into the detailed structure–property relationships, but also opens a new avenue for the rational design of efficient fluorescent sensors for NO detection.