New dual conjugated polymer electrochromic device with remarkable yellow-to-green switch for adaptive camouflage

Syntheses of novel fluorinated dibenzo[a,c]phenazine comprising polymers for electrochromic device applications

“…Tributyl(4-hexylthiophen-2-yl)stannane (6) and tributyl(2,3-dihydrothieno [3,4-b][1,4]dioxin-5-yl)stannane (7) were synthesized according to literature procedures. [38][39][40] Phenanthrene-9,10-dione (1) was brominated with N-bromosuccinimide (NBS).…”

“…41 4-Fluoro-2nitroaniline (3) was reduced to 4-fluorobenzene-1,2-diamine (4) reacted with 2,7-dibromophenanthrene-9,10-dione (2) to synthesize 2,7-dibromo-11-fluorodibenzo[a,c]phenazine (5). 42 Compound 5 was coupled with tributyl(4-hexylthiophen-2-yl)stannane (6) via Stille cross-coupling to afford 11-fluoro-2,7-bis(4-hexylthiophen-2yl)dibenzo[a,c]phenazine (TFBPz). Bromination of compound 8 was performed in the presence of NBS and CHCl 3 to synthesize 2,7bis(5-bromo-4-hexylthiophen-2-yl)-11-fluorodibenzo[a,c]phenazine (9).…”

“…Synthesis of 11-fluoro-2,7-bis(4-hexylthiophen-2-yl) dibenzo[a,c]phenazine (TFBPz). 2,7-Dibromo-11-fluorodibenzo-[a,c]phenazine (500 mg, 1.09 mmol) (5) and tributyl(4-hexylthio-phen-2-yl)stannane(1.5 g, 3.30 mmol) (6) were dissolved in anhydrous THF. The solution was degassed with argon for 30 minutes and then tris(dibenzylideneacetone) dipalladium(0) (50 mg, 5.5 mmol) and tri(o-tolyl)-phosphine (134 mg, 43.6 mmol) were added to the reaction mixture quickly to avoid exposure to oxygen.…”

“…[1][2][3][4][5] The discovery of these fascinating, multifunctional materials has opened a new research area and several researchers are focused on the field of conjugated polymers and their potential usage in different application areas such as electrochromic devices (ECDs), organic photovoltaics (OPVs), organic light emitting diodes (OLEDs), field effect transistors (FETs), biosensors, and super capacitors (SCs). [6][7][8][9][10][11][12][13][14] There are some crucial parameters for conjugated polymers such as the band gap (E g ), absorption in the visible region and energy levels. The Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) affect the performance of conducting polymers (CPs) in these applications.…”

“…1–5 The discovery of these fascinating, multifunctional materials has opened a new research area and several researchers are focused on the field of conjugated polymers and their potential usage in different application areas such as electrochromic devices (ECDs), organic photovoltaics (OPVs), organic light emitting diodes (OLEDs), field effect transistors (FETs), biosensors, and super capacitors (SCs). 6–14…”