Vinylene-linked Diketopyrrolopyrrole Chromophores for Electrochromism

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Mar 27

PMID 38533099

Authors

Vinutha K V

Rajeswara Rao M

Affiliations

Soon will be listed here.

Abstract

We report a novel series of vinylene-linked DPP compounds (1-5) formed Knoevenagel condensation of dimethyl DPP (6) with various aromatic aldehydes. Incorporating the vinylene linkage and photo- and electro-active groups offered the distinct advantage of extending π-delocalization, resulting in deep-coloured solids with absorption maxima extending to 620-680 nm and low redox potentials. The DPP-triphenylamine compound (5) showed electrochromism in the near-infrared region. The colour of the solution changed from blue to green, and the absorption from 680 nm to 740 nm, leading to NIR-to-NIR absorption switching. This system exhibits rapid switching, swift response times (1.4 s and 1.2 s), and reversibility in electrochromic behaviour.

References

Hang Y, Wang J, Jiang T, Lu N, Hua J . Diketopyrrolopyrrole-Based Ratiometric/Turn-on Fluorescent Chemosensors for Citrate Detection in the Near-Infrared Region by an Aggregation-Induced Emission Mechanism. Anal Chem. 2016; 88(3):1696-703. DOI: 10.1021/acs.analchem.5b03715. View

Bao W, Li R, Dai Z, Tang J, Shi X, Geng J . Diketopyrrolopyrrole (DPP)-Based Materials and Its Applications: A Review. Front Chem. 2020; 8:679. PMC: 7511705. DOI: 10.3389/fchem.2020.00679. View

Hupfer M, Koszarna B, Ghosh S, Gryko D, Presselt M . Langmuir-Blodgett Films of Diketopyrrolopyrroles with Tunable Amphiphilicity. Langmuir. 2021; 37(34):10272-10278. DOI: 10.1021/acs.langmuir.1c01113. View

Gu C, Jia A, Zhang Y, Zhang S . Emerging Electrochromic Materials and Devices for Future Displays. Chem Rev. 2022; 122(18):14679-14721. PMC: 9523732. DOI: 10.1021/acs.chemrev.1c01055. View

Dhar J, Mukhopadhay T, Yaacobi-Gross N, Anthopoulos T, Salzner U, Swaraj S . Effect of Chalcogens on Electronic and Photophysical Properties of Vinylene-Based Diketopyrrolopyrrole Copolymers. J Phys Chem B. 2015; 119(34):11307-16. DOI: 10.1021/acs.jpcb.5b03145. View

More K, Mirgane H, Shaikh S, Perupogu V, Birajdar S, Puyad A . 2-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor. J Org Chem. 2022; 89(9):5917-5926. DOI: 10.1021/acs.joc.2c01439. View

Tang A, Zhan C, Yao J, Zhou E . Design of Diketopyrrolopyrrole (DPP)-Based Small Molecules for Organic-Solar-Cell Applications. Adv Mater. 2016; 29(2). DOI: 10.1002/adma.201600013. View

Kim Y, Li X, Kim K, Kim S, Moon H . Tetrathiafulvalene: effective organic anodic materials for WO-based electrochromic devices. RSC Adv. 2022; 9(34):19450-19456. PMC: 9065372. DOI: 10.1039/c9ra02840d. View

Ghosh S, Raveendran R, Saeki A, Seki S, Namboothiry M, Ajayaghosh A . Charge Carrier Polarity Modulation in Diketopyrrolopyrrole-Based Low Band Gap Semiconductors by Terminal Functionalization. ACS Appl Mater Interfaces. 2018; 11(1):1088-1095. DOI: 10.1021/acsami.8b16714. View

10.

Tatemura R, Yasutake M, Kinoshita H, Miura K . Electrochemical Properties and Electrochromism of 6-Aryl-1,3-bis(trimethylsilyl)fulvenes and Their Derivatives. J Org Chem. 2021; 87(1):172-183. DOI: 10.1021/acs.joc.1c02133. View

11.

Pieczykolan M, Derr J, Chrayteh A, Koszarna B, Clark J, Vakuliuk O . The Synthesis and Photophysical Properties of Weakly Coupled Diketopyrrolopyrroles. Molecules. 2021; 26(16). PMC: 8398321. DOI: 10.3390/molecules26164744. View

12.

Kaur M, Choi D . Diketopyrrolopyrrole: brilliant red pigment dye-based fluorescent probes and their applications. Chem Soc Rev. 2014; 44(1):58-77. DOI: 10.1039/c4cs00248b. View

13.

Burckstummer H, Weissenstein A, Bialas D, Wurthner F . Synthesis and characterization of optical and redox properties of bithiophene-functionalized diketopyrrolopyrrole chromophores. J Org Chem. 2011; 76(8):2426-32. DOI: 10.1021/jo2003117. View

14.

Wang C, Qin Y, Sun Y, Guan Y, Xu W, Zhu D . Thiophene-Diketopyrrolopyrrole-Based Quinoidal Small Molecules as Solution-Processable and Air-Stable Organic Semiconductors: Tuning of the Length and Branching Position of the Alkyl Side Chain toward a High-Performance n-Channel Organic.... ACS Appl Mater Interfaces. 2015; 7(29):15978-87. DOI: 10.1021/acsami.5b04082. View

15.

Cui B, Zhong Y, Yao J . Three-state near-infrared electrochromism at the molecular scale. J Am Chem Soc. 2015; 137(12):4058-61. DOI: 10.1021/jacs.5b00586. View

16.

Kim J, Park J, Yang H, Jung I, Yoon S, Kim D . Controlling the Morphology of BDTT-DPP-Based Small Molecules via End-Group Functionalization for Highly Efficient Single and Tandem Organic Photovoltaic Cells. ACS Appl Mater Interfaces. 2015; 7(43):23866-75. DOI: 10.1021/acsami.5b05248. View

17.

Jeong Y, Lee C, Jang W . A diketopyrrolopyrrole-based colorimetric and fluorescent probe for cyanide detection. Chem Asian J. 2012; 7(7):1562-6. DOI: 10.1002/asia.201101038. View

18.

Feng D, Barton G, Scott C . Synthesis of 2,5-Dibutyl-3,6-dimethyl-1 H,2 H,4 H,5 H-pyrrolo[3,4- c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds. Org Lett. 2019; 21(7):1973-1978. DOI: 10.1021/acs.orglett.9b00019. View

19.

Wang L, Lai B, Ran X, Tang H, Cao D . Recent Advances of Diketopyrrolopyrrole Derivatives in Cancer Therapy and Imaging Applications. Molecules. 2023; 28(10). PMC: 10221687. DOI: 10.3390/molecules28104097. View

20.

Hwang T, Kim J, Namgoong J, Lee J, Yuk S, Kim S . Aggregation induced emission of diketopyrrolopyrrole (DPP) derivatives for highly fluorescent red films. Photochem Photobiol Sci. 2019; 18(5):1064-1074. DOI: 10.1039/c8pp00403j. View