Photochromism is a term that describes the photoreversible isomerization between two different states or isomers with distinct performances. Among all the photochromic molecule family, diarylethene is considered one of the most popular star molecules on account of its fast photoresponsibility, excellent thermal stability, fatigue resistance, high photoreaction quantum yield, and conversion ratio as well as good performances in both solution and solid phases. In the past decades, the development of diarylethene is witnessed in molecule design, solution applications, surface/interface assembly, bulky crystals and polymers, optic‐electronic devices fabrication, and biotechnology. This review mainly focuses on the latest development of diarylethenes in recent five years and commences with the newly designed molecular structures with functional ethene bridges and aryl moieties. The application of diarylethenes in materials science, soft materials, molecular data processing, and biomaterials, is further discussed in prospect. A brief summary is given in the end of the review together with some perspectives.

The Endeavor of Diarylethenes: New Structures, High Performance, and Bright Future

Photopolymerization, or the use of light to trigger polymerization, is one of the most exciting technologies for advanced manufacturing of polymers. One of the key components in the photopolymerization processes is the photoactive compound that absorbs the light, generating the active species that promotes the polymerization and largely determines the final properties of the material. The field of photopolymerization has been dominated by photoradical generators to mediate radical reactions. In the last decade, to expand the number of polymers that can be prepared by photopolymerization, intensive research has been devoted to the synthesis and utilization of photoactive molecules that are able to generate a base or an acid upon irradiation. These organic compounds are known to promote not only the ring-opening polymerization of various heterocyclic monomers such as lactones, carbonates, or epoxides but also to trigger the step-growth synthesis of polyurethanes. This Minireview highlights the recent advances in the development of organic photobase and photoacid generators, with the aim of encouraging the wider application of these photoactive compounds in the photopolymerization area and to expand the use of these polymers in advanced manufacturing processes.

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Recent Advances and Challenges in the Design of Organic Photoacid and Photobase Generators for Polymerizations.

This review focuses upon major achievements and recent advancements in the development of photoactive molecules which, under controlled illumination, release acidic groups either in solution or at the solid state. Successful photoacid generators are described the design of which are based on ionic, benzyl ester, imino ester, spiropyran and terarylene frameworks and the mechanism of acid generation in each case is discussed in detail. The development of such systems towards applications in lithography, surface etching, polymer design and two photon absorption processes are presented in order to give a state of the art overview of the development of new photoacid generators in the last three decades.

Recent progress in development of photoacid generators

A series of novel photochromic thieno[3,2-b]phosphole oxides has been shown to demonstrate photochromism without the need for the use of high-energy ultraviolet (UV) light irradiation while maintaining promising photochromic properties such as excellent thermal irreversibility, robust fatigue resistance, and high photoswitching efficiency. Promising visible light-induced photochromic properties have been realized by the new molecular design, in which various π systems have been incorporated into the weakly aromatic phosphole backbone instead of the conventional modification of the peripheral diaryl units that usually leads to a drastic reduction of the photochromic quantum yields (ϕO→C and ϕC→O < 0.01) or even a loss of the photochromic behavior. Excellent fatigue resistance has been observed for a representative compound with no apparent loss of photochromic reactivity over ten photochromic cycles by alternate irradiation with violet (ca. 410 nm) and green (ca. 500 nm) light with high photochromic quantu...

Photochromic Heterocycle-Fused Thieno[3,2-b]phosphole Oxides as Visible Light Switches without Sacrificing Photoswitching Efficiency

For a long time, starting from pioneering works of M. Irie in the late 80 s and early 90 s of the last century, photochromic diarylethenes were primarily associated with dithienylethenes – diarylethenes possessing thiophene groups. However, about 10 years ago, azole heterocycles (thiazole, oxazole, imidazole) started to be used as aryl moieties instead of common thiophenes, which contributed significantly to the development of diarylethene-based photochromes. In this review, we analyzed in detail the effects of substituting traditional thiophenes in diarylethenes by azoles and revealed amazing examples of functional molecules, materials, and devices based on azole-containing photochromic molecules.

Azole-based diarylethenes as the next step towards advanced photochromic materials

We herein propose a new type of efficient neutral photoacid generator. A photoinduced 6π-electrocyclization reaction of photochromic triangle terarylenes triggers subsequent release of a Bronsted acid, which took place from the photocyclized form. A H-atom and its conjugate base were introduced at both sides of a 6π-system to form the self-contained photoacid generator. UV irradiation to the 6π-system produces a cyclohexa-1,3-diene part with a H-atom and a conjugate base on the sp3 C-atoms at 5- and 6-positions, respectively, which spontaneously release an acid molecule quantitatively forming a polyaromatic compound. A net quantum yield of photoacid generation as high as 0.52 under ambient conditions and a photoinitiated cationic polymerization of an epoxy monomer are demonstrated.

Self-Contained Photoacid Generator Triggered by Photocyclization of Triangle Terarylene Backbone

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Self-Contained Photoacid Generator Triggered by Photocyclization of Triangle Terarylene Backbone