Vinylene-linked diketopyrrolopyrrole chromophores for electrochromism

K. V., Vinutha; M., Rajeswara Rao

doi:10.1039/d4ra01280a

RSC Adv.

2024

DOI: 10.1039/d4ra01280a

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Vinylene-linked diketopyrrolopyrrole chromophores for electrochromism

Vinutha K. V.,

Rajeswara Rao M.

Abstract: Novel series of vinylene-linked DPP compounds were synthesized via Knoevenagel condensation of dimethyl DPP (6) with various aromatic aldehydes. The compounds are redox active and exhibit reversible electrochromism with NIR-to-NIR switching.

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Electron‐Deficient Indenofluorene‐Based Systems: Multicolor and Visible‐To‐Near‐Infrared (NIR) Electrochromism and OFF‐OFF‐ON Electrofluorochromism

Nipate,

Kamble,

Rao

2024

Chemistry An Asian Journal

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Here, we report the synthesis and multi‐functional electrochromic behaviour (multi‐colour modulation, visible‐to‐near IR absorption switching, and electrofluorochromism) of electron‐deficient indenofluorene‐based systems. The compounds (IF1‐IF5) have been obtained via Knoevenagel condensation of indenofluorenone (IFK) with various nucleophiles (malononitrile, benzylcyanide, dimethyl malonate, methyl cyanoacetate, benzothiazole‐2‐acetonitrile). IF1‐IF5 possess strong colours and absorb in the visible region (λmax = 295‐388 nm). These compounds are electroactive and exhibit two reversible reduction waves (‐0.35 ̶ ‐0.88 V and ‐0.65 ̶ ‐1.30V vs Ag/AgCl), generating radical anion and dianion systems. For the electrochromic studies, upon applying the one‐electron reduction potential (‐0.35 V vs Ag/AgCl), the absorption maximum of IF1 redshift from 382 nm to 1240 nm (IF1‐•), which subsequently blueshifts to 466 & 745 nm (IF12‐•) upon increasing to two‐electron reduction potential (‐0.65 V vs Ag/AgCl). The color of the solution was switched from green to dark blue and further to light orange. The electrochromic behaviour is highly reversible and cycling. In addition, unlike the non‐fluorescent (IF1 and IF1‐•), the two‐electron reduced system (IF12‐•) is red‐emissive (λem = 630 nm) due to the combination of radicals leading to the formation of antiaromatic quinoidal π‐conjugated system (IF12‐).

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Electron‐Deficient Indenofluorene‐Based Systems: Multicolor and Visible‐To‐Near‐Infrared (NIR) Electrochromism and OFF‐OFF‐ON Electrofluorochromism

Nipate,

Kamble,

Rao

2024

Chemistry An Asian Journal

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Near-IR absorbing tetraene-linked π-conjugated porous polymers for energy storage and electrical conductivity

Venkatareddy,

Parsimehr,

Ignaszak

et al. 2025

Chem. Commun.

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Vinylene-linked diketopyrrolopyrrole chromophores for electrochromism

Abstract: Novel series of vinylene-linked DPP compounds were synthesized via Knoevenagel condensation of dimethyl DPP (6) with various aromatic aldehydes. The compounds are redox active and exhibit reversible electrochromism with NIR-to-NIR switching.

Cited by 2 publications

References 43 publications

Electron‐Deficient Indenofluorene‐Based Systems: Multicolor and Visible‐To‐Near‐Infrared (NIR) Electrochromism and OFF‐OFF‐ON Electrofluorochromism

Electron‐Deficient Indenofluorene‐Based Systems: Multicolor and Visible‐To‐Near‐Infrared (NIR) Electrochromism and OFF‐OFF‐ON Electrofluorochromism

Near-IR absorbing tetraene-linked π-conjugated porous polymers for energy storage and electrical conductivity

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