“Colorless-to-Black” Electrochromic and AIE-Active Polyamides: An Effective Strategy for the Highest-Contrast Electrofluorochromism

Abstract

Electrofluorochromic (EFC) materials have gained extensive attention owing to their interesting modulations of fluorescence by an electric stimulus. However, the limited performances, especially the low fluorescence on/off contrast, significantly hampered their further applications. Herein, we design a new strategy to achieve high-contrast electrofluorochromism by combinations of “colorless-to-black” electrochromism and highly fluorescent AIE activity. Given the effective fluorescence quenching effect and high solid-state fluorescence, a fluorescence contrast of 838 is realized, to the best of our knowledge, the highest reported so far. Furthermore, to explore the structure–property relationships, we also separated the E/Z isomers of tetraphenylethylene (TPE) and studied the properties of the three electroactive/fluorescent polymers (11TPE-PA, E-12TPE-PA, and Z-12TPE-PA) derived from different TPE derivatives and isomers. The three branches of polymers all exhibited AIE-active and “colorless-to-black” electrochromic (EC) properties. In addition to the ultrahigh fluorescence contrast, Z-12TPE-PA also integrated high electrochromic contrast (Δ% T = 92%), short response time (0.6 s/0.3 s), and excellent switching stability (300 cycles), paving the way for the applications in various electronic applications. The study will provide novel insights into the future design and development of high-performance EC/EFC materials.

Recent advances of carbonyl olefination via McMurry coupling reaction

“…McMurry coupling reaction is also used to synthesize tetraphenylethylene (TPE) derivatives, 160 and 162, as a candidate for electrochromic (EC) and aggregation-induced emission (AIE)-polyamide materials. 93,94 The McMurry reaction produces olens with a mixture of E and Z isomers which are difficult to separate. To respond to these problems, adding certain functional groups to TPE can cause polarity differences between the E and Z isomers.…”

Preparation and Chiral Applications of Optically Active Polyamides

“…[118,119] It is noteworthy that polyamides with fluorescent properties have been widely studied in recent years. [120][121][122] Accordingly, the introduction of fluorescent unit into chiral polyamides may lead to new advanced chiral materials that combine the advantages of chirality and fluorescence, which are expected to find applications in chiralassociated areas.…”

Photoinduced E to Z isomerization of tetraphenylethylene derivatives within organometallic supramolecular assemblies

“…Disubstituted TPE derivatives are conventionally synthesized by the McMurry coupling of unsymmetrically sybstituted ketones. This protocol normally yields a mixture of E-and Z-isomers (Scheme 1) [29][30][31][32]. Separation of these isomers by column chromatography proved difficult owing to the similarity in the properties of the isomers [29][30][31][32][33].…”

“…This protocol normally yields a mixture of E-and Z-isomers (Scheme 1) [29][30][31][32]. Separation of these isomers by column chromatography proved difficult owing to the similarity in the properties of the isomers [29][30][31][32][33]. Increasing the difference in polarity of the isomers is the usual but not the only method to achieve separation of the isomers [9,34].…”