Isomerically Pure Anthra[2,3‑<i>b</i>:6,7‑<i>b</i>′]-difuran (<i>anti</i>-ADF), -dithiophene (<i>anti</i>-ADT), and -diselenophene (<i>anti</i>-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

A new straightforward synthesis of isomerically pure anthra­[2,3-<i>b</i>:6,7-<i>b</i>′] -difuran (<i>anti</i>-ADF), -dithiophene (<i>anti</i>-ADT), and -diselenophene (<i>anti</i>-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped <i>anti</i>-acenedichalcogenophene compounds, that is, benzo­[1,2-<i>b</i>:4,5-<i>b</i>′]-, naphtho­[2,3-<i>b</i>:6,7-<i>b</i>′]-, and anthra­[2,3-<i>b</i>:6,7-<i>b</i>′]- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent <i>anti</i>-anthradichalcogenophenes, <i>anti</i>-ADT and <i>anti</i>-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm² V^–1 s^–1 for ADT and 0.7 cm² V^–1 s^–1 for ADS. The mobility of isomerically pure <i>anti</i>-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of <i>anti</i>-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm² V^–1 s^–1

Isomerically Pure Anthra[2,3‑<i>b</i>:6,7‑<i>b</i>′]-difuran (<i>anti</i>-ADF), -dithiophene (<i>anti</i>-ADT), and -diselenophene (<i>anti</i>-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

A new straightforward synthesis of isomerically pure anthra­[2,3-<i>b</i>:6,7-<i>b</i>′] -difuran (<i>anti</i>-ADF), -dithiophene (<i>anti</i>-ADT), and -diselenophene (<i>anti</i>-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped <i>anti</i>-acenedichalcogenophene compounds, that is, benzo­[1,2-<i>b</i>:4,5-<i>b</i>′]-, naphtho­[2,3-<i>b</i>:6,7-<i>b</i>′]-, and anthra­[2,3-<i>b</i>:6,7-<i>b</i>′]- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent <i>anti</i>-anthradichalcogenophenes, <i>anti</i>-ADT and <i>anti</i>-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm² V^–1 s^–1 for ADT and 0.7 cm² V^–1 s^–1 for ADS. The mobility of isomerically pure <i>anti</i>-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of <i>anti</i>-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm² V^–1 s^–1

Transparent and Nonflammable Ionogel Photon Upconverters and Their Solute Transport Properties

Photon upconversion based on triplet–triplet annihilation (TTA-UC) is a technology to convert presently wasted sub-bandgap photons to usable higher-energy photons. In this paper, ionogel TTA-UC samples are first developed by gelatinizing ionic liquids containing triplet-sensitizing and light-emitting molecules using an ionic gelator, resulting in transparent and nonflammable ionogel photon upconverters. The photophysical properties of the ionogel samples are then investigated, and the results suggest that the effect of gelation on the diffusion of the solutes is negligibly small. To further examine this suggestion and acquire fundamental insight into the solute transport properties of the samples, the diffusion of charge-neutral solute species over much longer distances than microscopic interpolymer distances is measured by electrochemical potential-step chronoamperometry. The results reveal that the diffusion of solute species is not affected by gelation within the tested gelator concentration range, supporting our interpretation of the initial results of the photophysical investigations. Overall, our results show that the advantage of nonfluidity can be imparted to ionic-liquid-based photon upconverters without sacrificing molecular diffusion, optical transparency, and nonflammability