A NIR dye with high-performance n-type semiconducting properties

Xie, Jiajun; Shi, Ke; Cai, Kang; Zhang, Di; Wang, Jieyu; Pei, Jian; Zhao, Dahui

doi:10.1039/c5sc03045e

Cited by 54 publications

(30 citation statements)

References 37 publications

(16 reference statements)

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“…Although calculations predict that the dimers should be significantly twisted (dihedral angle between 111° and 123°), OTFTs still exhibit promising performances (Table S2, Supporting Information). Furthermore, a chemically fused dimer, SM13, was reported by Pei and Zhao; calculations suggested that this dimer should be close to coplanar. This molecule exhibited a remarkably low LUMO level of −4.72 eV, measured by cyclic voltammetry, in combination with a low optical bandgap close to 1.1 eV.…”

Section: N‐type Organic Semiconductorsmentioning

confidence: 99%

Recent Progress in High‐Mobility Organic Transistors: A Reality Check

et al. 2018

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Over the past three decades, significant research efforts have focused on improving the charge carrier mobility of organic thin-film transistors (OTFTs). In recent years, a commonly observed nonlinearity in OTFT current-voltage characteristics, known as the "kink" or "double slope," has led to widespread mobility overestimations, contaminating the relevant literature. Here, published data from the past 30 years is reviewed to uncover the extent of the field-effect mobility hype and identify the progress that has actually been achieved in the field of OTFTs. Present carrier-mobility-related challenges are identified, finding that reliable hole and electron mobility values of 20 and 10 cm V s , respectively, have yet to be achieved. Based on the analysis, the literature is then reviewed to summarize the concepts behind the success of high-performance p-type polymers, along with the latest understanding of the design criteria that will enable further mobility enhancement in n-type polymers and small molecules, and the reasons why high carrier mobility values have been consistently produced from small molecule/polymer blend semiconductors. Overall, this review brings together important information that aids reliable OTFT data analysis, while providing guidelines for the development of next-generation organic semiconductors.

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Section: N‐type Organic Semiconductorsmentioning

confidence: 99%

Recent Progress in High‐Mobility Organic Transistors: A Reality Check

et al. 2018

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“…They found that the maximum absorption energy decreased linearly versus the inverse square length of the conjugated system, and the absorption maxima of pentarylenediimide and hexarylenediimide were at 877 and 953 nm, respectively . Nevertheless, there has been limited number of successful examples of stable NIR absorption molecules through extending the π‐system utilizing polycyclic units because: 1) the conjugation saturation usually appears with band gap higher than 1.4 eV in many previously reported studies, attributing to the effective conjugated length (ECL) effect; 2) to narrow the band gap, the lowest unoccupied molecular orbital (LUMO) has to be lowered and/or the highest occupied molecular orbital (HOMO) energy level elevated; however, over‐elevating the HOMO would induce the instability of the compounds in air; and 3) the construction of elongated fused aromatics remains highly challenging owing to the tediousness of synthetic chemistry and poor solubility of the products.…”

Section: Methodsmentioning

confidence: 99%

Fused Isoindigo Ribbons with Absorption Bands Reaching Near‐Infrared

et al. 2018

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Through fusing isoindigo (IID) units at 6,7;6′,7′‐positions, a series of new near‐infrared (NIR) absorbing and stable ribbon‐like conjugated molecules, namely nIIDs in which n represents the number of IID units, have been synthesized. The optical band gaps of the molecules are lowered from 2.03 eV of 1IID to 1.12 eV of 6IID with the increase of the conjugation length. 3IID, 4IID, and 6IID have strong absorption in the NIR region and exhibit photothermal conversion efficiencies of greater than 50 % under laser irradiation at λ=808 nm.

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“…Thec yclic voltammograms of both compounds showed four reversible reduction peaks with the first half-wave potentials at À0.87 V for 5 and À0.68 Vfor 6 vs.Fc/Fc + ,suggesting strong electronaccepting ability.T he LUMO levels were determined to be À4.10 eV for 5 and À4.27 eV for 6,from the onset potentials of the first reduction peaks,i mplying potential air-stable ntype semiconductors. [16] Theenergy gap E g estimated from the edge of the absorption spectra in CHCl 3 is 2.12 eV for 5 and 1.83 eV for 6.C alculations of nuclear independent chemical shifts (NICS) at the DFT-PBE0/6-31G(d) level indicate that the naphthalene subunits with imide groups show aromatic character whereas the naphthalene subunits with annulated benzene rings exhibit an antiaromatic feature and the annulated benzene rings exhibit aromaticity (Figure 4).…”

Section: Methodsmentioning

confidence: 99%

A Decatwistacene with an Overall 170° Torsion

Fan¹,

Winands²,

Doltsinis³

et al. 2017

Angewandte Chemie

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Tw od ifferent lengths of twistacenes,n amely hexatwistacene and decatwistacene,i nduced by steric hindrance between imide groups and neighboring annulated benzene rings,w ere synthesized by bottom-up synthesis of palladium-catalyzedS uzuki cross-coupling and CÀHa ctivation. Singlecrystal X-ray analyses revealed that decatwistacene,w hichi s the longest twistacene reported, exhibits an astonishing overall end-to-end torsion angle of about 1708 8,the largest torsion angle reported. Both twistacenes have an enhanced solubility and stability with respect to light and oxygen owingt ot heir large twisting deformations together with muchlower LUMO levels caused by the introduction of imide groups,opening awindow to the narrowest chiral graphene nanoribbons with good stability and processability.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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A NIR dye with high-performance n-type semiconducting properties

Abstract: A novel hetero-polycyclic aromatic compound showing strong NIR absorption and high-performance n-type semiconducting properties is developed. A special metal-free C–C coupling serves as a pivotal step in constructing the polycyclic π-framework.

Cited by 54 publications

References 37 publications

Recent Progress in High‐Mobility Organic Transistors: A Reality Check

Recent Progress in High‐Mobility Organic Transistors: A Reality Check

Fused Isoindigo Ribbons with Absorption Bands Reaching Near‐Infrared

A Decatwistacene with an Overall 170° Torsion

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