From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

Tam, Teck Lip Dexter; Salim, Teddy; Li, Hairong; Zhou, Feng; Mhaisalkar, Subodh; Su, Haibin; Lam, Yeng Ming; Grimsdale, Andrew C.

doi:10.1039/c2jm33317a

Cited by 28 publications

(11 citation statements)

References 37 publications

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“…4,7-Di(thiophen-2-yl)-2,1,3-benzothiadiazole (DTBT) is very commonly used as the electron withdrawing unit in donoracceptor based small molecules and polymers for both OPV and OFET applications. 3,[18][19][20] Different derivatives of the 2,1,3benzothiadiazole unit, such as naphtho [1,2-c:5,6-c]bis [1,2,5] thiadiazole (NBT), 21,22 benzobisthiadiazole (BBT) [23][24][25][26] and thiadiazoloquinoxaline (TQ) [27][28][29][30][31] have been synthesised in order to increase the electron deciency. Polymers containing TQ units have shown ambipolar charge transport with electron mobilities up to 0.04 cm 2 V À1 s À1 .…”

Section: Introductionmentioning

confidence: 99%

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

et al. 2015

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“…Electron-deficient (hetero)aromatic moieties are key components of n-type organic semiconducting materials. − Various electron acceptor moieties such as dicyanovinylene, − diketopyrrolopyrrole (DPP), , [1,2,5]-thiadia-zolo[3,4-g]quinoxaline (TQ), − benzothiadiazole (BT), perylene diimide (PDI), − naphthalene diimide (NDI), and isoindigo (IID) have already been developed. Among them, BT is a particularly popular case and has been introduced into oligomers and polymers for use in (opto)electronic devices. ,− Moreover, some other BT derivatives, such as thiazole-fused BTs, , thiadiazolopyridine, , and thiadiazoloquinoxaline have also been synthesized, which largely enriched the BT-based electron acceptors.…”

Section: Introductionmentioning

confidence: 99%

Fused Bis-Benzothiadiazoles as Electron Acceptors

Xia

Guo

Baumgarten

et al. 2016

Crystal Growth & Design

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Fused bis-benzothiadiazoles with different molecular geometries, namely, linear benzoquinone-fused bis(benzothiadiazole) (Q-BBT) and V-shaped sulfone-fused bis(benzothiadiazole) (S-BBT), were synthesized. Single crystal analysis of Q-BBT and S-BBT revealed profoundly distinct packing modes, which must be ascribed to the different molecular shapes. Experimental and theoretical studies indicated that both compounds give rise to electron-accepting materials. This work thus also contributes to the diversity of electron acceptors based on bis-benzothiadiazole moieties and highlights the important role of molecular shape for the solid-state packing of organic conjugated materials.

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“…While much research on VLG DA polymers has been focused on OFETs and OSCs, ,, very little has been done to characterize the electrochromism aspect of these polymers . Since DA polymers have access to multiple redox states in a small potential window, these materials can be potentially useful in electrochromic devices, supercapacitors, batteries, and sensors .…”

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confidence: 99%

Very Low Band Gap Thiadiazoloquinoxaline Donor–Acceptor Polymers as Multi-tool Conjugated Polymers

et al. 2014

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Here we report on the synthesis of two novel very low band gap (VLG) donor-acceptor polymers (Eg ≤ 1 eV) and an oligomer based on the thiadiazoloquinoxaline acceptor. Both polymers demonstrate decent ambipolar mobilities, with P1 showing the best performance of ∼10(-2) cm(2) V(-1) s(-1) for p- and n-type operation. These polymers are among the lowest band gap polymers (≲0.7 eV) reported, with a neutral λmax = 1476 nm (P2), which is the farthest red-shifted λmax reported to date for a soluble processable polymer. Very little has been done to characterize the electrochromic aspects of VLG polymers; interestingly, these polymers actually show a bleaching of their neutral absorptions in the near-infrared region and have an electrochromic contrast up to 30% at a switching speed of 3 s.

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From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

Cited by 28 publications

References 37 publications

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

Fused Bis-Benzothiadiazoles as Electron Acceptors

Very Low Band Gap Thiadiazoloquinoxaline Donor–Acceptor Polymers as Multi-tool Conjugated Polymers

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