Novel core-substituted naphthalene diimide-based conjugated polymers for electrochromic applications

Wang, Kai; Zhu, Lin; Hu, Xuening; Han, Mingxi; Lin, Junyu; Guo, Zhiyong; Zhan, Hongbing

doi:10.1039/d1tc04446j

Cited by 13 publications

(3 citation statements)

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“…The electrochromic behavior of poly(DTP-NDI) described in this research is in line with previous reports of electrochromism of -(D-A-D)- polymers consisting of the naphthalene diimide acceptor and carbazole, 38 triphenylamine, 80 or phenothiazine 81 donors. All of these polymers exhibit a rich color palette originating from the fact that due to their ambipolar nature, their electrochromism can exploit different oxidation as well as reduction states.…”

Section: Resultssupporting

confidence: 92%

D-A-D Compounds Combining Dithienopyrrole Donors and Acceptors of Increasing Electron-Withdrawing Capability: Synthesis, Spectroscopy, Electropolymerization, and Electrochromism

et al. 2022

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Five D-π-A-π-D compounds consisting of the same donor unit (dithieno[3,2- b :2′,3′- d ]pyrrole, DTP ), the same π-linker (2,5-thienylene), and different acceptors of increasing electron-withdrawing ability (1,3,4-thiadiazole ( TD ), benzo[ c ][1,2,5]thiadiazole ( BTD ), 2,5-dihydropyrrolo[3,4- c ]pyrrole-1,4-dione ( DPP ), 1,2,4,5-tetrazine ( TZ ), and benzo[ lmn ][3,8]phenanthroline-1,3,6,8(2 H ,7 H )-tetraone ( NDI )) were synthesized. DTP-TD , DTP-BTD , and DTP-DPP turned out to be interesting luminophores emitting either yellow ( DTP-TD) or near-infrared ( DTP-BTD and DTP-DPP ) radiation in dichloromethane solutions. The emission bands were increasingly bathochromically shifted with increasing solvent polarity. Electrochemically determined electron affinities (|EA|s) were found to be strongly dependent on the nature of the acceptor changing from 2.86 to 3.84 eV for DTP-TD and DTP-NDI , respectively, while the ionization potential (IP) values varied only weakly. Experimental findings were strongly supported by theoretical calculations, which correctly predicted the observed solvent dependence of the emission spectra. Similarly, the calculated IP and EA values were in excellent agreement with the experiment. DTP-TD , DTP-BTD , DTP-TZ , and DTP-NDI could be electropolymerized to yield polymers of very narrow electrochemical band gap and characterized by redox states differing in color coordinates and lightness. Poly(DTP-NDI) and poly(DTP-TD) showed promising electrochromic behavior, not only providing a rich color palette in the visible but also exhibiting near-infrared (NIR) electrochromism.

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Section: Resultssupporting

confidence: 92%

D-A-D Compounds Combining Dithienopyrrole Donors and Acceptors of Increasing Electron-Withdrawing Capability: Synthesis, Spectroscopy, Electropolymerization, and Electrochromism

et al. 2022

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“…[54,394,395] Some eminent examples of electrochemically redox active molecules are derivatives of tetrathiafulvalene, [396,397] ferrocene [398,399] (and other metallocenes), anthraquinone, [400,401] benzodifuran [402] or viologen [403,404] (Figure 12A), as well as more sophisticated molecules such as redox-active proteins, [405,406] transition metal complexes, [407] macrocycles, [408,409] and metalorganic frameworks. [410,411] It is also worth to mention electrochromic molecules (or electrophores), a specific type of redox-responsive molecules that can reversibly generate optical variations (e.g., color, fluorescence, transparency) in response to an external bias potential, highlighting Prussian blue (hexacyanoferrate), [412] diimides, [413] and viologens, [414] being the latest the only electrochromic organic molecule exploited in commercial applications so far. Otherwise, some nonredox active molecules can also modify the electron transport when exposed to an electric field; nonetheless, that kind of switches are typically promoted in solid state, but not in solution.…”

Section: Redox-responsive Moleculesmentioning

confidence: 99%

Rational Design of Stimuli‐Responsive Inorganic 2D Materials via Molecular Engineering: Toward Molecule‐Programmable Nanoelectronics

Muñoz

2023

Advanced Materials

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The ability of electronic devices to act as switches makes digital information processing possible. Succeeding graphene, emerging Inorganic 2D Materials (i2DMs) have been identified as alternative 2D Materials to harbor a variety of active molecular components to move the current silicon‐based semiconductor technology forward to a post‐Moore era based on molecule‐based information processing components. In this regard, i2DMs benefits not only for their prominent physiochemical properties (e.g., the existence of band gap, contrary to graphene), but also their high surface‐to‐volume ratio rich in reactive sites (functionalization capability). Nonetheless, since this field is still in an early stage, having knowledge of both i) the different strategies for molecularly functionalizing the current library of i2DMs, and ii) the different types of active molecular components is a sine qua non condition for a rational design of stimuli‐responsive i2DMs capable of performing logical binary operations at the molecular level. Consequently, this Review provides a comprehensive tutorial for covalently anchoring ad hoc molecular components —as active units triggered by different external inputs— onto pivotal i2DMs to assess their role in the expanding field of Molecule‐Programmable Nanoelectronics for electrically monitoring bistable molecular switches. Limitations, challenges, and future perspectives of this emerging field which crosses materials chemistry with computation are critically discussed.This article is protected by copyright. All rights reserved

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“…Currently, NDIs have been extensively used in organic field-effect transistors (OFETs) and photovoltaic (OPV) applications as air-stable, n-type semiconductors . The ability to change both color and redox properties without global structural changes is one of the most attractive characteristics of cNDIs. − More interestingly, the planar face-to-face π-stacking structure and high π-acidity of cNDIs are theoretically facile to construct layered COFs, which will facilitate the above-mentioned study.…”

mentioning

confidence: 99%

Design, Synthesis, and Ultrafast Carrier Dynamics of Core-Substituted Naphthalene Diimide-Based Covalent Organic Frameworks

Luo,

Chang,

Pei

et al. 2023

Nano Lett.

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A series of two-dimensional polyimide covalent organic frameworks (2D COF) based on core-substituted naphthalene diimides (cNDIs) were designed and synthesized with the characteristic of tunable bandgap without global structural changes. Cyclic voltammetry (CV) and DFT calculations indicated that COFcNDI‑OEt and COFcNDI‑SEt possess higher HOMO/LUMO levels and narrower bandgaps than COFNDI‑H. Further investigation indicated that the COF bandgaps are not only related to the electron-donating substituents but also varied with respect to the interlayer distances. Moreover, the femtosecond transient absorption (TA) spectra manifested that the electron donor substituents are beneficial to the charge delocalization in the π-columnar unit, resulting in a longer lifetime of charge recombination, which is one of the pivotal prerequisites for high-performance solar cells and photocatalysis.

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Novel core-substituted naphthalene diimide-based conjugated polymers for electrochromic applications

Abstract: The strategic implementation of using a core-substituted naphthalene diimide derivative to electropolymerize an ionized polymer for a better electrochromic performance is proposed.

Cited by 13 publications

References 44 publications

D-A-D Compounds Combining Dithienopyrrole Donors and Acceptors of Increasing Electron-Withdrawing Capability: Synthesis, Spectroscopy, Electropolymerization, and Electrochromism

D-A-D Compounds Combining Dithienopyrrole Donors and Acceptors of Increasing Electron-Withdrawing Capability: Synthesis, Spectroscopy, Electropolymerization, and Electrochromism

Rational Design of Stimuli‐Responsive Inorganic 2D Materials via Molecular Engineering: Toward Molecule‐Programmable Nanoelectronics

Design, Synthesis, and Ultrafast Carrier Dynamics of Core-Substituted Naphthalene Diimide-Based Covalent Organic Frameworks

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