Propylene and butylene glycol: new alternatives to ethylene glycol in conjugated polymers for bioelectronic applications

Moser, Maximilian; Wang, Yazhou; Castillo, Tania Cecilia Hidalgo; Liao, Hailiang; Yu, Yikai; Chen, Junxin; Duan, Jiayao; Moruzzi, Floriana; Griggs, Sophie; Marks, Adam; Gasparini, Nicola; Wadsworth, Andrew; Inal, Sahika; McCulloch, Iain; Yue, Wan

doi:10.1039/d1mh01889b

Cited by 29 publications

(32 citation statements)

References 54 publications

(82 reference statements)

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“…Over the past few years, polar and hydrophilic oligo ethylene glycol (OEG) side chains modified conjugated polymers as the channel layers have been developed rapidly, [ 14–17 ] particularly for p‐type (hole transport) OECT devices with the μC* figure of merit up to ≈563 F V −1 cm −1 s −1 given by pgBTTT . [ 18–21 ] Whereas n‐type OECTs are yet much more immature than their p‐type counterparts owing to the lacking of rational n‐type design principles, although several types of n‐type polymeric structures have shown a figure of merit μC* more than 1 F V −1 cm −1 s −1 , [ 22–24 ] most of which presented unsatisfactory performance. [ 25,26 ] This unbalanced situation greatly precludes the development of the lower power consumption complementary circuits and hinders the diversity of bioelectronics applications where n‐type mixed conductors are demanded.…”

Section: Introductionmentioning

confidence: 99%

“…Over the past few years, polar and hydrophilic oligo ethylene glycol (OEG) side chains modified conjugated polymers as the channel layers have been developed rapidly, [14][15][16][17] particularly for p-type (hole transport) OECT devices with the μC* figure of merit up to ≈563 F V −1 cm −1 s −1 given by pgBTTT. [18][19][20][21] Whereas n-type OECTs are yet much more immature than…”

Section: Introductionmentioning

confidence: 99%

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Highly Efficient Mixed Conduction in N‐type Fused Small Molecule Semiconductors

Duan

Zhu

Wang

et al. 2022

Adv Funct Materials

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Highly efficient mixed ionic and electronic conduction is critical to developing high‐performance organic electrochemical transistors (OECTs) devices. While currently, the n‐type small molecules mixed conductors design strategy remains extremely lacking. Herein, ethylene glycol (EG) chain substituted electron‐deficient naphthalene bis‐isatin and rhodanine acceptor units with easily accessible steps are rationally fused, affording fused and planar novel semiconductors with weak intramolecular S–O ‘conformation locks', where gNR with EG side chain and hgNR with hybrid alkyl‐EG side chain. The rigid, planar and highly electron‐deficient skeleton enables the resulting small molecule semiconductors to be efficient mixed ionic‐electronic conductors with very high OECT electron mobility up to 0.01 cm2 V−1 s−1. Remarkedly, gNR displays the record value of geometry‐normalized transconductance of 0.4 S cm−1 and μC* of 2.6 F V−1 cm−1 s−1, which can also be compared with the state‐of‐art n‐type semiconducting polymers in OECTs. Moreover, the effect of the alkyl spacer on the n‐type mixed ionic and electronic conduction features of the small molecule materials is investigated. The fused electron‐deficient acceptor‐acceptor (A–A) system with intramolecular conformation lock design strategy in this work provides a new avenue to realize next‐generation high‐performance small molecule mixed ionic and electronic conductors for OECT materials.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Efficient Mixed Conduction in N‐type Fused Small Molecule Semiconductors

Duan

Zhu

Wang

et al. 2022

Adv Funct Materials

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“…[10,11] Aqueous-based electrolyte has been reported as a promising alternative to organic electrolytes owing to its beneficial properties, such as incombustibility, high ionic conductivity, and low manufacturing cost coming from air insensitivity. [12,13] Therefore, aqueous media has great potential to develop nontoxic, environment-friendly electrochemical devices, such as biosensors, [14] organic electrochemical transistors (OECTs), [15] energy-storage devices, [16] electrochromic devices (ECDs) [17] and organic electronic ion pumps (OEIPs). [18] However, most common D-A copolymers are hydrophobic which originate from alkyl side chains and building blocks.…”

Section: Introductionmentioning

confidence: 99%

Donor Functionalization Tuning the N‐Type Performance of Donor–Acceptor Copolymers for Aqueous‐Based Electrochemical Devices

Cong

Chen

Wang

et al. 2022

Adv Funct Materials

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In this work, three n‐type donor–acceptor copolymers consisting of glycolated naphthalene tetracarboxylicdiimide (gNDI) coupled with variable donating companion moieties are reported. Using 2,2′‐bis(3,4‐ethylenedioxy)bithiophene, 2,2′‐bithiophene, 3,3′‐difluoro‐2,2′‐bithiophene (FBT), the donating strength of the donor units is systematically functionalized. These copolymers are used as a platform for aqueous‐based electrochemical devices, including energy‐storage devices, electrochromic devices (ECDs), and organic electrochemical transistors (OECTs). It is found that the electrochemical redox stability and electron mobility of copolymers are significantly improved via weakening the electron‐donating strength of donor units. gNDI coupling with FBT (gNDI‐FBT) exhibits a charge‐storage capacity exceeding 190 Fg−1, which is the highest value reported to date for NDI‐based polymer electrodes in aqueous media. For ECDs, gNDI‐FBT remains 100% of initial electrochromism contrast (∆%T = 20%) up to 1200 s. In addition, gNDI‐FBT outperforms its two analogs in OECTs, including lower threshold voltage (0.19 V), faster response time (45.5 ms), and higher volumetric capacitance (197 F cm−3). Moreover, gNDI‐FBT with fluorine atoms leads to the bipolarons delocalization along the polymer backbone and favorable molecular packing for ion–electron transport. Through such weak donor functionalization strategy, this work provides ways for n‐type copolymers tuning to access desirable performance metrics in optical, electrochemical, and bioelectronic applications.

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“…[21] Other studies with spacers ranging from C 3 to C 6 groups in n-type and thiophene homopolymers have shown that excessive swelling can be reduced to improve electronic charge transport. [22,23] The alkyl-group spacers have also shown promise in thermoelectric applications, where the Seebeck coefficient is increased without diminishing energetic order. [24] Another strategy is tuning the conjugated backbone structure of polymers from homopolymers such as poly(3-hexylthiophene) (P3HT) to donor-acceptor (D-A) type copolymers.…”

Section: Introductionmentioning

confidence: 99%

The Role of Long‐Alkyl‐Group Spacers in Glycolated Copolymers for High‐Performance Organic Electrochemical Transistors

Kim

Stewart

et al. 2022

Advanced Materials

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Semiconducting polymers with oligoethylene glycol (OEG) sidechains have attracted strong research interest for organic electrochemical transistor (OECT) applications. However, key molecular design rules for high-performance OECTs via efficient mixed electronic/ionic charge transport are still unclear. In this work, new glycolated copolymers (gDPP-TTT and gDPP-TTVTT) with diketopyrrolopyrrole (DPP) acceptor and thiophene (T) and vinylene (V) thiophene-based donor units are synthesized and characterized for accumulation mode OECTs, where a long-alkyl-group (C 12 ) attached to the DPP unit acts as a spacer distancing the OEG groups from the polymer backbone. gDPP-TTVTT shows the highest OECT transconductance (61.9 S cm -1 ) and high operational stability, compared to gDPP-TTT and their alkylated counterparts. Surprisingly, gDPP-TTVTT also shows high electronic charge mobility in a field-effect transistor, suggesting efficient ion injection/diffusion without hindering its efficient electronic charge transport. The elongated donor unit (TTVTT) facilitates hole polaron formation to be more localized to the donor unit, leading to faster and easier polaron formation with less impact on polymer structure during OECT operation, as opposed to the TTT unit. This is supported by molecular dynamics simulation. These simultaneously high electronic and ionic charge-transport properties are achieved due to the long-alkyl-group spacer in amphipathic sidechains, providing an important molecular design rule for glycolated copolymers.

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Propylene and butylene glycol: new alternatives to ethylene glycol in conjugated polymers for bioelectronic applications

Abstract: Propylene and butylene glycol oligoether chains have been employed as alternatives to ethylene glycol in thiophene based semiconductors for OECTs. Their impact on electrochemical, microstructure, and swelling properties are discussed.

Cited by 29 publications

References 54 publications

Highly Efficient Mixed Conduction in N‐type Fused Small Molecule Semiconductors

Highly Efficient Mixed Conduction in N‐type Fused Small Molecule Semiconductors

Donor Functionalization Tuning the N‐Type Performance of Donor–Acceptor Copolymers for Aqueous‐Based Electrochemical Devices

The Role of Long‐Alkyl‐Group Spacers in Glycolated Copolymers for High‐Performance Organic Electrochemical Transistors

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