Cholesterol-substituted 3,4-ethylenedioxythiophene (EDOT-MA-cholesterol) and Poly(3,4-ethylenedioxythiophene) (PEDOT-MA-cholesterol)

Wu, Yuhang; Nagane, Samadhan S.; Baugh, Quintin; Lo, Chen‐Tsyr; Chhatre, Shrirang; Lee, Jung-Hyun; Sitarik, Peter; Kayser, Laure V.; Martin, David C.

doi:10.1016/j.giant.2023.100163

Cited by 2 publications

(7 citation statements)

References 76 publications

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“…Importantly, we also showcased the ability of EDOT-MA monomers to be modified with a range of biomolecules and amino acids like cholesterol, adamantane, and cysteine. We also demonstrated that these modified monomers retain their ability to be polymerized electrochemically …”

Section: Introductionmentioning

confidence: 78%

“…We also demonstrated that these modified monomers retain their ability to be polymerized electrochemically. 25 We have also demonstrated that polymers made from racemic EDOT-MA (PEDOT-MA) form continuous films that show improved capacitive behavior. 4 The UV absorbance of these polymers is similar to that of unmodified PEDOT, indicating the formation of an extended molecular conjugation.…”

Section: Introductionmentioning

confidence: 95%

“…We also demonstrated that these modified monomers retain their ability to be polymerized electrochemically. 25 …”

Section: Introductionmentioning

confidence: 99%

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Influence of Controlled Chirality on the Crystallization of Maleimide-Functionalized 3,4-Ethylenedioxythiophene (EDOT-MA) Monomers

Chhatre,

Nagane,

et al. 2024

ACS Omega

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Conjugated poly(alkoxythiophenes) such as poly-(3,4-ethylenedioxythiophene) (PEDOT) have attracted considerable interest for use in a variety of applications such as biomedical devices, energy storage, and chemical sensing. Functionalized versions of the 3,4-ethylenedioxythiophene (EDOT) monomer make it possible to create polymers with properties tailored for specific applications. The maleimide functional group shows particular promise due to the wide variety of chemical modifications that it can undergo. Here, we examine the role that control of the chirality of the maleimide (MA) substituent has on the crystal structure and crystallization of the EDOT-MA monomer. We describe a method for the synthesis of a homochiral (S) variant of EDOT-MA and compare its crystallography, morphology, and thermal properties to that of the (R,S) EDOT-MA racemic compound. The conformation of the EDOT-MA molecule was substantially different, with the molecules adopting an "L" shape in the homochiral crystal, while in the racemic crystals, they were more colinear. The thermal stability of the homochiral crystals (T m = 128.6 °C) was slightly higher than the racemic ones (T m = 102.8 °C). We expect these results to be important in better understanding the solid-state assembly of the corresponding polymers prepared from these monomers.

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Section: Introductionmentioning

confidence: 78%

Section: Introductionmentioning

confidence: 95%

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Influence of Controlled Chirality on the Crystallization of Maleimide-Functionalized 3,4-Ethylenedioxythiophene (EDOT-MA) Monomers

Chhatre,

Nagane,

et al. 2024

ACS Omega

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“…13 Additionally, pristine PEDOT lacks the suitable surface chemistry needed to properly interact with several biological targets. 19 Moreover, PEDOT:PSS presents disadvantages related to the acidity and toxicity of PSS, potentially triggering unsought reactions with materials adjacent to the active layer of the bioelectronic device. 20 Furthermore, the excess negative charge associated with PSS in the conducting polymer-polyelectrolyte complex limits its interaction with some proteins, nucleic acids, and cells, which are likewise negatively charged under physiological conditions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…21,23 Another effective approach involves synthesizing and subsequently polymerizing EDOT derivatives containing recognition motifs suitable for further bioconjugation. 19 In this regard, and over the past decades, several EDOT derivatives have been synthesized and investigated, such as PEDOT derivatized with phosphonate groups separated by methylene and butylene alkyl spacers (PEDOT-Phos and PEDOT-Bu-Phos), 24 PEDOT functionalized with maleimide moieties (PEDOT-MA) and also with cholesterol substitution (PEDOT-MAcholesterol), 19 PEDOT with pendant diethylene glycol moieties (PEDOT-DEG), 25 PEDOT with azide moieties (PEDOT-N 3 ), 26,27 and PEDOT with an alkylsulfonate chain (PEDOT-S), 28 among many other interesting examples. 29,30 On the other hand, click chemistry constitutes a collection of reactions characterized by their orthogonality, selectivity, and high-yield outcomes, all amenable to execution in aqueous solvents and at room temperature, and whose significance was distinguished by the 2022 Chemistry Nobel Prize.…”

Section: ■ Introductionmentioning

confidence: 99%

A Poly(3,4-ethylenedioxythiophene) Derivative Incorporating Ethynyl Moieties for Click Chemistry-Based Bioelectronics

Fenoy,

Lorenz,

Pasquale

et al. 2024

Chem. Mater.

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Efficiently integrating biological elements with the surface of organic semiconductors is a key objective in advancing the development of bioelectronic devices. In this work, we introduce the fabrication and functionalization of organic electrochemical transistors (OECTs) utilizing PEDOT-E as channel material, a poly(3,4ethylenedioxythiophene) (PEDOT) derivative featuring pendant ethynyl moieties. First, the synthesis of the EDOT-E monomer and its electropolymerization onto Au interdigitated electrodes to produce PEDOT-E OECTs are detailed. Next, the film growth process is investigated by varying the number of electropolymerization cycles, leading to the optimization of the transistor fabrication protocol. The obtained devices exhibit lower threshold voltage values compared with state-of-the-art PEDOT-based OECTs. Furthermore, the ethynyl moieties are exploited for the click chemistry-based functionalization of the devices, enabling the incorporation of ferrocene redox probes. Next, biorecognition elements such as an azide-functionalized biotin are also anchored, yielding the acquisition of robust bioconstructs based on avidin−biotin interactions that are suitable for enzymatic biosensing. Last, azido-functionalized gelatin is "clicked" onto the transistors, not only enhancing their electronic features but also improving their biocompatibility for cell interfacing, a crucial step toward the further development of neural probes.

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Cholesterol-substituted 3,4-ethylenedioxythiophene (EDOT-MA-cholesterol) and Poly(3,4-ethylenedioxythiophene) (PEDOT-MA-cholesterol)

Cited by 2 publications

References 76 publications

Influence of Controlled Chirality on the Crystallization of Maleimide-Functionalized 3,4-Ethylenedioxythiophene (EDOT-MA) Monomers

Influence of Controlled Chirality on the Crystallization of Maleimide-Functionalized 3,4-Ethylenedioxythiophene (EDOT-MA) Monomers

A Poly(3,4-ethylenedioxythiophene) Derivative Incorporating Ethynyl Moieties for Click Chemistry-Based Bioelectronics

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