New β-linked pyrrole monomers: approaches to highly stable and conductive electrochromic polymers

Trapping of Stable [4n+1] π‐Electron Species from Peripherally Substituted, Conformationally Rigid, Antiaromatic Hexaphyrins

“…For instance, an attempted oxidative coupling reaction of 1,2‐dipyrroyl benzene was reported in 2004 by Swager et al. ; however, they failed to isolate the desired product . More recently, Takase and co‐workers reported the synthesis of cyclophanes bearing a naphthobipyrrole moiety, and their report showed the importance of using an N‐protected 1,2‐di(pyrrolyl)benzene in the oxidative coupling process .…”

“…In fact, numerous attempts were made to effect the direct oxidative coupling of 7 to obtain the corresponding bipyrrole but without success. Notably, most of the reported oxidative coupling methods that might allow the conversion of 7 to 10 directly were not successful . However, a strategy that involved switching the protecting group from N ‐triisopropylsilyl ( N ‐TIPS) to N ‐ tert ‐butoxycarbonyl ( N ‐Boc), followed by oxidative coupling, afforded the coupled product 9 in clean form and in 77 % yield.…”

Metalated Heterocycles in Organic Synthesis: Recent Applications

“…206 When the boronic acid functionality in the protected pyrrole is desired at C-3, its preparation is achieved generally via a brominationlithiation-borination sequence, a recent example being the synthesis of a N-silyl-protected pyrrol-3-ylboronic acid, which has been employed in the synthesis of conductive electrochromic polymers. 207 N Boc …”

An experimental study of the electronic absorption and fluorescence spectral properties of new p-substituted-N-phenylpyrroles and their electrosynthesized polymers

“…COPs have been widely utilized in several fields, including semiconductors [4,5], sensors [6], water decontamination [7,8], and electrochromic devices (ECDs) [9][10][11]. In particular, polypyrrole (PPy) has been probably one of the most extensively used COPs for electrochromic materials as well as for energy storage and sensors, because of its many advantages, like simple chemical and electrochemical synthesis, environmental stability, processability, fast switching time, good electrical properties, long-term stable conductivity, and possible formation of homopolymers or composites with optimal mechanical properties [2,12,13]. However, PPy has also some well-known drawbacks, such as poor chemical and physical properties and, above all, insolubility in most common organic solvents, which greatly reduces the scope of practical applications, and especially complicates the study of optical properties in organic solutions.…”