Structure-activity And Application Performance Of Fluorescence Probe Regulated And Controlled By N/O Spiro-heterocycle

The original information of crucial importance in natural science always lurk in the micro-structure,and they often been captured,controlled and transformed by messenger molecule in the pattern of light.Light and light-based technology is alaways predictive to scientific problems and guiding them,which make molecule probe and photosensitive imaging technology become the key to break through.This dissertation is based on the challenging design and research of novel high-efficiency functional fluorescence molecules,promotes their optical properties,achieve information expression,transformation and application of molecule behavior,especially for complicated life system,environment system and medical diagnosis and treatment area,initiating novel broke though on numerous interdisciplinary subjects.Among multitudinous of fluorescence functional probe molecules,those use xanthene structure as the signal core and spiro-heterocycle as the drive have draw a lot of attentions due to their excellent dectection properties.In this dissertation,We have focused on the intergration of Organic synthetic chemistry,analytical chemistry,chemicobiology,theoretical and computational chemistry refer to numerous referrences,constructed four general categories of fluorescence functional probe molecules which are based on xanthene framework,and then put forword four functional expansion strategies on account of their structural characters.1)We have summarized the basic construction strategies of fluorescence functional probe molecules,and reviewed the research progress of construction and application in this area recently.2)We have used rhodamine as the signal output motif,constructed a serise of fluorescence functional probe molecules S1-S9 to detect Cu²⁺,which use nine different cinnamaldehyde derivatives as the recognition group induced by metal,regulated and controled by Schiff base and the xanthene“off-on”strategies.The influence of different substituent group have been investigated systematically upon their electronic effect and steric hindrance effect.Furthermore,this kind of probes could be used to detect Cu²⁺ in L929 cell.3)Guiding by practical effectiveness,we have assembled a serise of Sn4+ probes Z1-Z4 based on the construction core of thiadiazole derivatives,and the signal source of rhodanmine,which could be regulated and controled by steric hinerance effect.The recognition properties were dissected and their performance variation were illuminated by theoretical calculation simulation.Moreover,these probes could be used to detect Sn4+ in living Hela cells and KunMing mice and showed excellent preformance and made novel breakthrough.4)We have used ethane diamine flexible chain to combine rhodamine conjugated unit and benzoazoles recognition moiety to construct a series of fluorescent probe N1-N4 which have the ability to detect Al3+ in high concentration.Their recognition mechanism have been evidenced by theoretical calculation simulation.Also,we have investigate the detection properties of these probes for Al3+ in Hela cells and KunMing mice.5)We have designed and synthesized a series of fluorescence probe Y1-Y4 using fluorescein as luminous core based on protection-deprotection reaction mechanism.The recognition mechanism has been proved by theoretical calculation simulation on their reaction activities.Fukui function has been used to analyze the influence of the different position of electron donating group do to recognition properties of these probes,illuminate the relationship between their performance and structures,and then propose the construction method and control strategy.In summary,we have constructed four general categories of fluorescence functional probe molecules,with N/O heterocycle leuco structure at the core.The analysis of their optical recognition and detection properties,investigation of their recognition mechanism and extension of their biological application performance could provide guidance for the construction and application of fluorescence functional probe molecule.