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Abstract
Long-standing radical species have raised noteworthy concerns in organic functional chemistry and materials. However, there remains a substantial challenge to produce long-standing radicals by light, because of the structural dilemmas between photoproduction and stabilization. Herein, we present a pyrrole and chloride assisted photochromic structure to address this issue. In this well-selected system, production and stabilization of a radical species were simultaneously found accompanied by a photochemical process in chloroform. Theoretical study and mechanism construction indicate that the designed π-system provides a superior spin-delocalization effect and a large steric effect, mostly avoiding possible consumptions and making the radical stable for hours even under an oxygen-saturated condition. Moreover, this radical system can be applied for a visualized and quantitative detection towards peroxides, such as 2,2,6,6-tetramethylpiperidine-1-oxyl, hydrogen peroxide, and ozone. As the detection relies on a radical capturing mechanism, a higher sensing rate was achieved compared to traditional redox techniques for peroxide detection.
Highlights
Long-standing radical species have raised noteworthy concerns in organic functional chemistry and materials
We note that the photochromism, as a representative photochemical behavior, which can undergo rapid and efficient photocontrol process accompanied by dramatic π-electron rearrangement to change the apparent color[18,19,20,21,22,23], may have potential to fulfill the task
In summary, a unique stable radical formation strategy triggered by photochromism has been demonstrated
Summary
Long-standing radical species have raised noteworthy concerns in organic functional chemistry and materials. By delocalizing spin and blocking subsequent reactions, chemists have developed several molecular structures (e.g. multi-cyano skeletons[4], tetramethyl azacyclic systems[5], polythiophenes[6,7], azulenes[8], porphyrins[9], and other extended aromatic compounds10) for achieving stable radical species These systems show remarkable potential in organic optoelectronics, magnetic materials and magnetic resonance imaging, non-linear optical devices, as well as energy storage[11,12]. Dithienylethene is a typical photochromic moiety enabling a relatively large and planar molecular geometry during photocyclization[33,34] In another hand, pyrrole and chloride can work as effective assisted groups to stabilize the radicals in large π-conjugated systems[35,36]. We eventually find that the compound 1 can perform as we expected by optimization (Fig. 1b)
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