Tunable Photochromism of Spirooxazine in the Solid State: A New Design Strategy Based on the Hypochromic Effect

Abstract

As an important organic photofunctional material, spirooxazine (SO) usually does not exhibit photochromism in the solid state since the intermolecular π–π stacking impedes photoisomerization. Developing photochromic SO in the solid state is crucial for practical applications but is still full of challenges. Here, a series of spirooxazine derivatives (SO1–SO4) with bulky aromatic substituents at the 4‐ and 7‐positions of the skeleton, which provide them with a large volume with which to undergo solid‐state photochromism under mild conditions, is designed and synthesized. All the compounds SO1–SO4 exhibit tunable solid photochromism without ground colors, excellent fatigue resistance, and high thermal stability. Notably, it takes only 15 s for SO4 to reach the saturation of absorption intensity, thought to represent the fastest solid‐state photoresponse of spirooxazines. X‐ray crystal structures of the intermediate compound SO0 and the products SO1–SO2 as well as computational studies suggest that the bulky aromatic groups can lead to a hypochromic effect, allowing for the photochromism of SO in the solid state. The ideal photochromic properties of these spirooxazines open a new avenue for their applications in UV printing, quick response code, and related fields.

A route to carbon-sp3 bridging spiro-molecules: synthetic methods and optoelectronic applications

“…In addition to their application in the field of batteries, spiro molecules also hold significant potential in the field of organic luminescence. Yang et al 136 synthesized SO4 molecules by substituting the spirobifluorene (SBF) units at positions 4 and 7 of spirooxazine (SO0) (shown in Fig. 16e).…”

Recent Development of Photochromic Polymer Systems: Mechanism, Materials, and Applications

“…Photochromic polymers have numerous commercial applications beyond academic research. For instance, photochromic materials [ 127 ] can be utilized in smart windows, ophthalmic lenses [ 128 ], UV printing [ 129 ], and so on [ 130 ]. The commercialization of photochromic polymers remains a hot topic of current research.…”

Polyoxometalate/s-triazine hybrid heterostructures with ultrafast photochromic properties

“…1–4 In recent decades, researchers have dedicated substantial efforts to explore fast photo-responsive photochromic materials. 5,6 Among these materials, D–A hybrid heterostructures, which are composed of semiconductive organic and inorganic electron donors and acceptors self-assembled through supramolecular interactions, have emerged as ideal platforms for designing high-performance photochromic materials. 7–9 The advantages of D–A hybrid heterostructures in constructing photochromic materials with fast photo-responsiveness can be attributed to three factors.…”