In the past few years, spiropyran has emerged as the molecule-of-choice for the construction of novel dynamic materials. This unique molecular switch undergoes structural isomerisation in response to a variety of orthogonal stimuli, e.g. light, temperature, metal ions, redox potential, and mechanical stress. Incorporation of this switch onto macromolecular supports or inorganic scaffolds allows for the creation of robust dynamic materials. This review discusses the synthesis, switching conditions, and use of dynamic materials in which spiropyran has been attached to the surfaces of polymers, biomacromolecules, inorganic nanoparticles, as well as solid surfaces. The resulting materials show fascinating properties whereby the state of the switch intimately affects a multitude of useful properties of the support. The utility of the spiropyran switch will undoubtedly endow these materials with far-reaching applications in the near future.

/pdf/spiropyran-based-dynamic-materials-4c1onvrhup.pdf

Spiropyran-based dynamic materials

Organic photoresponse materials and devices are critically important to organic optoelectronics and energy crises. The activities of photoresponse in organic materials can be summarized in three effects, photoconductive, photovoltaic and optical memory effects. Correspondingly, devices based on the three effects can be divided into (i) photoconductive devices such as photodetectors, photoreceptors, photoswitches and phototransistors, (ii) photovoltaic devices such as organic solar cells, and (iii) optical data storage devices. It is expected that this systematic analysis of photoresponse materials and devices could be a guide for the better understanding of structure–property relationships of organic materials and provide key clues for the fabrication of high performance organic optoelectronic devices, the integration of them in circuits and the application of them in renewable green energy strategies (critical review, 452 references).

Organic photoresponse materials and devices

Organic semiconductors have garnered significant interest as key components for flexible, low-cost, and large-area electronics. Hitherto, both materials and processing thereof seems to head towards a mature technology which shall ultimately meet expectations and efforts built up over the past years. However, by its own organic electronics cannot compete or complement the silicon-based electronics in integrating multiple functions in a small area unless novel solutions are brought into play. Photochromic molecules are small organic molecules able to undergo reversible photochemical isomerization between (at least) two (meta)stable states which exhibit markedly different properties. They can be embedded as additional component in organic-based materials ready to be exploited in devices such as OLEDs, OFETs, and OLETs. The structurally controlled incorporation of photochromic molecules can be done at various interfaces of a device, including the electrode/semiconductor or dielectric/semiconductor interface, or even as a binary mixture in the active layer, in order to impart a light responsive nature to the device. This can be accomplished by modulating via a light stimulus fundamental physico-chemical properties such as charge injection and transport in the device.

25th Anniversary Article: Organic Electronics Marries Photochromism: Generation of Multifunctional Interfaces, Materials, and Devices

In order to perform chemical work, molecular systems have to be operated away from thermodynamic equilibrium and therefore require the input of energy. Light is perhaps the most abundant and advantageous energy source that in combination with photoswitches allows for a reversible and hence continuous stimulation of a system. In this review, we illustrate how photoswitchable molecules can be used to escape the global thermodynamic minimum by populating metastable states, from which energy can be transferred and transformed in a controlled fashion. We emphasize the unique feature of photodynamic equilibria, in which population of the states is dictated by the excitation wavelength (and not primarily by temperature), thereby avoiding microscopic reversibility since the photoreaction involves an electronically excited state. Thus, photoswitchable molecular systems can remotely be controlled with high spatial and temporal resolution and in addition their action can be fueled by light.

https://pubs.rsc.org/en/content/articlepdf/2017/cs/c7cs00112f?page=search

Photoswitchable molecules as key ingredients to drive systems away from the global thermodynamic minimum

Interface modification is an effective and promising route for developing functional organic field-effect transistors (OFETs). In this context, however, researchers have not created a reliable method of functionalizing the interfaces existing in OFETs, although this has been crucial for the technological development of high-performance CMOS circuits. Here, we demonstrate a novel approach that enables us to reversibly photocontrol the carrier density at the interface by using photochromic spiropyran (SP) self-assembled monolayers (SAMs) sandwiched between active semiconductors and gate insulators. Reversible changes in dipole moment of SPs in SAMs triggered by lights with different wavelengths produce two distinct built-in electric fields on the OFET that can modulate the channel conductance and consequently threshold voltage values, thus leading to a low-cost noninvasive memory device. This concept of interface functionalization offers attractive new prospects for the development of organic electronic dev...

Interface Engineering of Semiconductor/Dielectric Heterojunctions toward Functional Organic Thin-Film Transistors

A facile method to make optoelectronic devices formed from organic thin-film transistors that are functionalized by photochromic spiropyran dyes in a nondestructive manner has been developed. When PDMS stamps are employed, alkane-containing spiropyran molecules can be coated simply onto the surface of organic thin films in a noninvasive manner. Upon UV irradiation, the molecules undergo isomerization from the neutral closed form to the charge-separated merocyanine form, producing the local electrostatic environment. This photoinduced electrostatic environment can function as a local negative gate voltage, thus increasing the electrical conductivity in p-type devices and decreasing the electrical conductivity in n-type devices. Further irradiation with visible light or keeping the devices in the dark can switch the device conductance back to their initial value. This method is reversible and reproducible on different devices with different thickness over a long period of time.

Conformation-Induced Electrostatic Gating of the Conduction of Spiropyran-Coated Organic Thin-Film Transistors

Integrating Reaction Chemistry into Molecular Electron Devices

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Conformation-Induced Electrostatic Gating of the Conduction of Spiropyran-Coated Organic Thin-Film Transistors

Integrating Reaction Chemistry into Molecular Electron Devices