Optoelectronic Properties of Poly(2,5-dithienylpyrrole)s with Fluorophore Groups

Abstract

In this study two new, fluorophore anchored 2,5-dithienylpyrrole derivatives (SNS-Carb, SNS-Flo) were successfully synthesized via click chemistry. Both monomers were subjected to electrochemical polymerization and the corresponding polymers (PSNS-Carb and PSNS-Flo) were thoroughly characterized for their electrochromic properties. PSNS-Carb displayed yellow to blue coloration in 1.31 s with a coloration efficiency of 120 cm 2 C −1 whereas PSNS-Flo revealed longer switching time (2.67 s) and lower coloration efficiency (78 cm 2 C −1 ). Coexistence of 3,4-ethylenedioxythiophene (EDOT) with SNS-Carb or SNS-Flo in polymerization media resulted in the formation of novel copolymer films (P1 and P2, respectively) having entirely diverged multichromic, superior optoelectronic properties. P1 revealed a switching time of 1.33 s, with a coloration efficiency of 164 cm 2 C −1 , whereas P2 exhibited a slower response time (1.87 s) with a lower coloration efficiency (155 cm 2 C −1 ), as in the case of their respective homopolymers. In general, P1 was shown to reveal higher E values which indicate it's more noticeable and vivid color changing nature compared to P2. When the optoelectronic properties of homopolymers were compared with that of their respective copolymers, there was an explicit enhancement of the color pallet, switching time, optical contrast and coloration efficiency.

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

“…These characteristics have allowed the development of many technological applications [3], from organic and molecular electronic [4,5] to sensors [6][7][8] or smart surfaces [9][10][11][12][13]. Among many types of CPs, poly(thienyl-pyrrole-thienyl) derivatives have received great interest [14][15][16][17][18] especially for their electrochromic properties [19][20][21][22][23]. The structure of derivatives is generated from a central pyrrole units bearing two thiophene moieties attached on the C2 and C5 carbon atoms of the pyrrole and can be named SNS or Poly(SNS).…”

“…Moreover, many synthesis pathways have been developed to couple the SNS moieties and other monomers. Recently, Guven et al reported the synthesis of several SNS derivatives by click chemistry opening the way for new materials in electrochromic applications [20][21][22]. This approach allows one to achieve an effective post-polymerization functionalization of azide containing SNS monomer.…”

Electrochemical synthesis, optical, electrochemical and electrochromic characterizations of indene and 1,2,5-thiadiazole-based poly(2,5-dithienylpyrrole) derivatives

“…redox peaks with increasing scanning cycles could be related to formation of homopolymers and copolymers on the ITO electrode. 40 As shown in Fig. 2(a) and (b), the E onset , oxidation peak, and reduction peak of PDIT located at 0.68, 0.90, and 0.53 V, respectively, whereas those of PBDTA located at 0.73, 0.97, and 0.53 V, respectively.…”

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

“…Since the Paal-Knorr reaction can have relatively low yields, an innovative approach based on click chemistry has been proposed by our group leading to synthesis of SNS derivatives with substituted naphthalimide, 17 anthracene, 18 pyrene, 19 fluorene and carbazole units. 20 In addition, an ingenious approach, focused on click functionalization of the SNS polymer rather than the SNS monomer has been developed. Considering the poly SNS as an intermediate in the synthesis of the multifunctional final polymer, the modification taking place after the electrodeposition of the SNS structures allows flexibility in the selection of functional groups to be attached without regards to the limitations imposed by the Paal-Knorr type of synthesis.…”