Study On The Synthesis Of 9,10-bis-(Alkoxystyryl)anthracenes And Their Piezofluorochromism And Thermochromism

Since the finding of aggregation-induced emission phenomena, the applications of organic light-emitting materials with AIE property in high-tech fields have been intensively studied. Latest researches have demonstrated that most of the reported AIE organic compounds possess sensitive color-changing properties, which has greatly boosted their developments and applications in the fields of information recording, chemical sensors etc. Generally, 9,10-distyrylanthracene derivatives bearing twisted molecular backbones were reported to show AIE phenomena and sensitive color-changing properties, which made them become the focus of organic sensitive color-changing materials. Herein, a series of alkoxy-substituted 9,10-distyrylanthracene derivatives were synthesized, their AIE effect, piezofluorochromism and fluorescent thermochromism were examined, and their structure-property relationships were intensively investigated, the main contents and achievements are as follows:(1) The isomers(n-butyl, i-butyl and t-butyl at ortho or para positions) of 9,10-bis(butoxystyryl)anthracenes(DSA4) were designed and synthesized, the single crystals of DSA-pn4, DSA-pt4 and DSA-oi4 were successfully obtained. Being characterized by PL spectrum, all of the five isomers were found to show AIE property, in which DSA-pt4, DSA-on4, DSA-oi4 were found to exhibit obvious fluorescent color changes from yellow-green to yellow after pressing, indicating they are promising piezofluorochromic materials. Being characterized by DSC, WAXD and single crystal diffraction, we have investigated their structure-property relationships, proposed their piezofluorochromic mechanism and revealed that the isomerization of alkoxy group can effectively regulate the aggregation modes of DSA4, so as to further influence their optical properties and piezofluorochromism. The results provide a new method to design novel PAIE materials.(2) A series of 9,10-bis(p-alkoxystyryl)anthracenes(DSA-pnn) with different length of alkyl chains(n = 4, 8, 16) were designed and synthesized, and their single crystals were successfully obtained. Being characterized by PL spectrum, three DSA-pnn compounds were found to display obvious AIE phenomena and excellent fluorescent thermochromism, denoting they are promising fluorescent thermochromic materials. Being characterized by DSC, WAXD and single crystal diffraction, we have discussed their structure-property relationships, proposed their fluorescent thermochromic mechanism and explained the effect of length of periphery alkoxy group on optical properties and thermochromism of DSA-pnn, which provided references for follow-up researchers.