Photo-responsive perylene diimid–azobenzene dyad: Photochemistry and its morphology control by self-assembly

High-Performance Phototransistors Based on PDIF-CN2 Solution-Processed Single Fiber and Multifiber Assembly

“…Organic phototransistors, i.e., OFETs in which an incident light is used in addition to a gate field to modulate the charge-carrier density inside the channel, have many advantages over their inorganic counterparts, such as the tunability of their optoelectronic properties via the molecular design and their possibility to be assembled on nonplanar supports opening perspectives toward their flexible thus wearable applications. − Low-dimensional organic architectures such as crystalline micro/nanowire, − microribbon and quantum dot , structures have showed high photosensitivity and high charge carrier properties. Among organic semiconducting molecules used as active components in efficient phototransistors, perylene di-imide (PDI) derivatives are particularly suitable because of their characteristic absorption in the visible region combined with the capacity to transport electrons. − One of the major limitations of organic transistors, especially those based on n -type systems, is their air sensitivity. To overcome such a limitation, we have focused our attention on air-stable n -type perylene di-imide derivative, i.e., N , N ′-1H,1H-perfluorobutyl-dicyano perylene di-imide (PDIF-CN 2 ) (Figure ), which is known to form highly crystalline fibers by solvent-induced precipitation (SIP), being a simple solution-processable method to produce high-performing crystalline structures with respect to those that are vapor-grown.…”

Photomodulated Self-Assembly of Hydrophobic Thiol Monolayer-Protected Gold Nanorods and Their Alignment in Thermotropic Liquid Crystal

“… − Among the three thiols P n SHs, the intensity decrease of the azobenzene peak in P 4 SH with the shortest distance between PDI and azobenzene had the smallest change, whereas the P 8 SH with the longest distance between PDI and azobenzene had the largest change. This could be ascribed to the interaction between PDI and azobenzene groups, which lowered the degree of the trans – cis photoisomerization of azobenzene . This interaction could also reduce the photoluminescence of PDI.…”

“…This could be ascribed to the interaction between PDI and azobenzene groups, which lowered the degree of the trans−cis photoisomerization of azobenzene. 21 This interaction could also reduce the photoluminescence of PDI. P 4 SH displayed a red color, whereas P 6 SH and P 8 SH were yellow (insets in Figure 2, top).…”

Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads

“…20−25 Incorporating azo-side chains on PBIs showed intramolecular photoinduced electron transfer from the azo-side chain to the electron-deficient perylene backbone. 26,27 Also, we recently reported the photoinduced electron transfer from azobenzene guests to the perylene bisimide macrocycle hosts, which quenched the fluorescence and increased the stability of (Z)-azobenzene guests within the macrocycles. 28 The reported bay-functionalized perylene dyes show an efficient electron or energy transfer depending on the electronic nature of the substituents.…”

“…The azo-dyes are also used in optoelectronics, data storage, and biomedical applications owing to their stability, photoswitchability, and photoisomerization. − The azobenzene-substituted molecules undergo structural transformations such as isomerization, tautomerization, and electrocyclic ring closures and openings to control the structure and properties of supramolecular assemblies. − Incorporating azo-side chains on PBIs showed intramolecular photoinduced electron transfer from the azo-side chain to the electron-deficient perylene backbone. , Also, we recently reported the photoinduced electron transfer from azobenzene guests to the perylene bisimide macrocycle hosts, which quenched the fluorescence and increased the stability of ( Z )-azobenzene guests within the macrocycles . The reported bay-functionalized perylene dyes show an efficient electron or energy transfer depending on the electronic nature of the substituents. − For example, the oligothiophene-incorporated perylene bisimide compound produced supramolecular architectures with the photoinduced electron transfer from bithiophene groups to the perylene bisimide with photoconducting properties .…”