194416-45-0Relevant academic research and scientific papers
Arylamino-fluorene derivatives: Optically induced electron transfer investigation, redox-controlled modulation of absorption and fluorescence
Accorsi, Gianluca,Beneduci, Amerigo,Capodilupo, Agostina-Lina,Cardone, Antonio,Corrente, Giuseppina Anna,Fabiano, Eduardo,Giannuzzi, Roberto,Gigli, Giuseppe,Manni, Francesca
, (2020)
A series of biarylaminofluorene-based systems with donor-π-donor (D-π-D) structure have been designed and synthesized in order to study the dependence on the π-conjugated bridge length of the intervalence charge-transfer transitions (IV-CT) and of the electronic coupling between the redox centers. To this purpose cyclic voltammetry, UV/Vis-NIR, fluorescence spectroscopy and computational investigations have been carried out to characterize the electronic structure of the compounds in the neutral as well as in the mono- and dication states. Additionally, a study of related D-π compounds has been performed to elucidate the effect of the interaction between two redox centers. Interestingly it was observed that the mono- and dication species exhibit intense transition bands in the NIR region, in the 10000-15000 cm?1 range, whose intensity depends on the oxidation state and thus it can be reversibly tuned by an applied potential. In a similar way, all compounds show an oxidation state dependent fluorescence which leads to electrofluorochromism. Particularly significant is the mixed valence behavior that provides these systems singular optoelectronic properties, making them excellent active components for electrochromic and electrofluorochromic applications.
A Cost-Effective D-A-D Type Hole-Transport Material Enabling 20% Efficiency Inverted Perovskite Solar Cells?
Huang, Jiachen,Yang, Jie,Sun, Huiliang,Feng, Kui,Liao, Qiaogan,Li, Bolin,Yan, He,Guo, Xugang
, p. 1545 - 1552 (2021)
High-performance, cost-effective hole-transport materials (HTMs) are greatly desired for the commercialization of perovskite solar cells (PVSCs). Herein, two new HTMs, TPA-FO and TPA-PDO, are devised and synthesized, which have a donor-acceptor-donor (D-A-D) type molecule design featuring carbonyl group-functionalized arenes as the acceptor (A) units. The carbonyl group at the central core of HTMs can not only tune frontier molecular orbital (FMO) energy levels and surface wettability, but also can enable efficient surface passivation effects, resulting in reduced recombination loss. When employed as HTMs in inverted PVSCs without using dopant, TPA-FO with one carbonyl group yields a high power conversion efficiency (PCE) of 20.24%, which is among the highest values reported in the inverted PVSCs with dopant-free HTMs. More importantly, the facile one-step synthetic process enables a low cost of 30 USD g–1 for TPA-FO, much cheaper than the most studied HTMs used for high-efficiency dopant-free PVSCs. These results demonstrate the potential of D-A-D type molecules with carbonyl group-functionalized arene core in developing the low-cost dopant-free HTMs toward highly efficient PVSCs.
Acene-based organic semiconductors for organic light-emitting diodes and perovskite solar cells
Pham, Hong Duc,Hu, Hongwei,Wong, Fu-Lung,Lee, Chun-Sing,Chen, Wen-Cheng,Feron, Krishna,Manzhos, Sergei,Wang, Hongxia,Motta, Nunzio,Lam, Yeng Ming,Sonar, Prashant
, p. 9017 - 9029 (2018)
In this work, three novel acene-based organic semiconductors, including 2,7-bis(trimethylstannyl)naphtho[2,1-b:6,5-b′]dithiophene (TPA-NADT-TPA), 4,4′-(anthracene-2,6-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) (TPA-ANR-TPA) and N2,N2,N6,N6-tetrakis(4-methoxyphenyl)anthracene-2,6-diamine (DPA-ANR-DPA), are designed and synthesized for use in organic light-emitting diodes (OLEDs) and perovskite solar cells (PSCs). In OLEDs, devices based on TPA-NADT-TPA, TPA-ANR-TPA and DPA-ANR-DPA showed pure blue, blue green, and green emission, respectively. Also, the maximum brightness of the devices with a turn-on voltage of 3.8 V reached 8682 cd m-2 for TPA-NADT-TPA, 11180 cd m-2 for TPA-ANR-TPA, and 18 600 cd m-2 for DPA-ANR-DPA. These new materials are also employed as hole transporting materials (HTMs) in inverted PSCs, where they were used without additives. The inverted devices based on these HTMs achieved an overall efficiency of 10.27% for TPA-NADT-TPA, 7.54% for TPA-ANR-TPA, and 6.05% for DPA-ANR-DPA under identical conditions (AM 1.5G and 100 mW cm-2). While the PSCs with TPA-NADT-TPA as the HTM achieved the highest efficiency, the DPA-ANR-DPA-based OLED devices showed the brightest emission and efficiency. Based on the obtained promising performance, it is clear that this molecular design presents a new research strategy to develop materials that can be used in multiple types of devices.
New quinacridone derivatives: Synthesis, photophysical and third-order nonlinear optical properties
Feng, Dong,Jia, Jianhong,Liang, Guanqiu,Sha, Yangcheng,She, Yuanbin,Zhou, Chunsong
, (2020)
A series of quinacridone third-order nonlinear optical chromophores containing phenyl, 4-methoxyphenyl and N,N-bis(4-methoxyphenyl)aniline groups were designed and synthesized. The optical properties, electrical properties, theoretical calculations and Z-Scan of the compounds were measured and analyzed to investigate the relationship between structure and third-order NLO properties. The experimental results showed that the introduction of electron-donating groups at the N-position of quinacridone decreases the energy gap (Egap) between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the molecule, and promotes intramolecular charge transfer (ICT). Quinacridone derivatives containing N, N-bis (4-methoxyphenyl) aniline have good third-order nonlinear optical properties, with the nonlinear absorption coefficient (β) value of 1.4319 × 10?13 and the second-order superpolarizability (γ) of 2.6849 × 10?33 esu.
A novel dibenzimidazole-based fluorescent probe with high sensitivity and selectivity for copper ions
Ban, Xinxin,Li, Liantai,Li, Wen,Liu, Yan,Pan, Jie,Qiu, Suyu,Yu, Hui,Yu, Jianmin,Zhu, Aiyun
, (2021)
A novel fluorescence probe TPA-BMZ for Cu2+, based on intramolecular charge transfer, was designed and synthesized. Probe was composed of triphenylamine as the fluorophore and benzimidazole derivative as the receptor. AFM measurement exhibits that TPA-BMZ possess an amorphous state without any crystallization, which benefits to its long-term stability due to application. Meanwhile, its optical character was studied and the results shown that TPA-BMZ could be used to recognize cupric ions in consequence of intramolecular charge transfer (ICT) and it even could be used to detect the presence of cupric ions in seawater. The Job's plot curve demonstrated the molar ratio of probe to copper is 1:1. Moreover, from the fluorescence titration spectrum of copper ions to probe, the limit of detection of probe is obtained (0.094 μM) and the complex constant is 6.57 × 10?8 M?1 which shows a high sensibility towards copper ions. In addition, probe was also used to detect copper ions in tap water, river water and seawater which demonstrated a potential application in seawater. More importantly, the response time of the probe to copper ions is within 1 s.
The effect of the number, position, and shape of methoxy groups in triphenylamine donors on the performance of dye-sensitized solar cells
Kim, Se Hun,Choi, Jun,Sakong, Chun,Namgoong, Jin Woong,Lee, Woosung,Kim, Dong Hoe,Kim, Boeun,Ko, Min Jae,Kim, Jae Pil
, p. 390 - 401 (2015)
Four new organic photosensitizers (SH-11～14) that introduced methoxy groups as an additional donor were synthesized, and used in dye-sensitized solar cells. The dyes were designed in order to investigate the effects on the dye photophysical properties and the cell photovoltaic performance, by the number, position, and shape of methoxy groups introduced at the para-/ortho- and para-/meta- and para-(open or closed ring shape) positions on the triphenylamine donor. The introduction of methoxy groups led to bathochromic shift of the absorption spectrum, and enhancement of the molar extinction coefficient of the dyes. Their introduction decreased the amount of dye adsorbed on TiO2surface, due to the increased steric hindrance. As their number increased, an open-circuit voltage value decreased. All things considered, the dye (SH-14) with closed ring shape shows the best conversion efficiency of 6.01% under AM 1.5G conditions (N719 dye's 7.59% under the same conditions).
Benzotriazole-containing donor-acceptor-acceptor type cyclometalated iridium(III) complex for solution-processed near-infrared polymer light emitting diodes
Yu, Junting,Tan, Hua,Meng, Fanyuan,Lv, Kun,Zhu, Weiguo,Su, Shijian
, p. 231 - 238 (2016)
A novel near-infrared-emitting cyclometalated iridium(III) complex of (CH3OTPA-BTz-Iq)2Irpic containing benzotriazole unit with a donor-acceptor-acceptor (D-A-A) chromophore was synthesized and characterized. The optophysical, electrochemical and electroluminescent characteristics were primarily studied. A near-infrared emission peaked at 716 nm with a shoulder at 790 nm was exhibited in the (CH3OTPA-BTz-Iq)2Irpic dichloromethane solution at 298 K. In its optimized solution-processed polymer light-emitting diodes, a near-infrared electroluminescent emission peaked at 723 nm with a shoulder at 780 nm was observed with a maximum external quantum efficiency of 0.41% at 8.14 mA cm-2. This work indicates that introducing appropriate D and A units to develop D-A-A structure is an efficient approach to construct near-infrared-emitting iridium(III) complex in the polymer light-emitting diodes with suppressive efficiency roll-off.
Chemically Altering the Solubility and Durability of Dyes for Sensitized Solar Cells
Maniam, Subashani,Holmes, Andrew B.,Leeke, Gary A.,Bilic, Ante,Collis, Gavin E.
, p. 4022 - 4025 (2015)
By designing dyes with fluoroalkyl groups, the optical and electronic properties of the alkyl analogue were maintained while dramatically altering the solubility. Dyes, F-TABTA (8) and its masked derivative F-TABTSi (9), that enable them to be deposited under conventional organic solvent and scCO2 conditions, respectively, were developed. In liquid DSSC devices, the fluoroalkyl dye (F-TABTA, 8) performs slightly better than its alkyl analogue (D21L6, 10), and interestingly, it was found that the former device showed better stability over time. Deploying the silyl-masked precursor F-TABTSi (9), this dye was deposited onto TiO2 photoanodes from scCO2 in very short contact times (2.5 h), and ECEs of 7.70% were obtained that exceed the performance of the alkyl dye when deposited by conventional methods.
Boosting inverted perovskite solar cell performance by using 9,9-bis(4-diphenylaminophenyl)fluorene functionalized with triphenylamine as a dopant-free hole transporting material
Pham, Hong Duc,Gil-Escrig, Lidón,Feron, Krishna,Manzhos, Sergei,Albrecht, Steve,Bolink, Henk J.,Sonar, Prashant
, p. 12507 - 12517 (2019)
In this study, two newly developed small molecules based on 9,9-bis(4-diphenylaminophenyl)fluorene functionalized with triphenylamine moieties, namely TPA-2,7-FLTPA-TPA and TPA-3,6-FLTPA-TPA, are designed, synthesized and characterized. The electrochemical, optical and thermal properties of both materials are investigated using various techniques. Afterwards, these materials are employed as dopant-free hole transporting materials (HTMs) in planar inverted perovskite solar cell devices with the aim of determining the device performance and studying their stability in comparison with reference N4,N4,N4′′,N4′′-tetra([1,10-biphenyl]-4-yl)-[1,1′:4′,1′′-terphenyl]-4,4′′-diamine (TaTm)-based devices. Under 1 sun conditions, TPA-3,6-FLTPA-TPA-based devices achieve a power conversion efficiency (PCE) of 13.9% whereas TPA-2,7-FLTPA-TPA-based devices exhibit the highest PCE of 17.1% mainly due to an improvement in the fill factor (FF). Meanwhile, the devices prepared using TaTm as the reference HTM exhibit an overall efficiency of 15.9%. In addition to the higher efficiency, our newly developed HTM TPA-2,7-FLTPA-TPA-based devices demonstrate good stability which is comparable to those with TaTm under similar aging test conditions.
A novel perylenediimide molecule: Synthesis, structural property relationship and nanoarchitectonics
Siddiqui, Afzal,Thawarkar, Sachin,Singh, Surya Prakash
, (2021/11/22)
A novel perylene diimide derivative (1) was synthesized by Stille coupling protocol to examine the effect of bulky group attached at bay position on the formation of nano-architectonics of PDI derivatives. The compound 1 was self-assembled by fast injection of chloroform solution in methanol to give nano-architecture. The size, shape and morphology of nano-architectonics were elucidated by combination of different experimental techniques such as UV–Vis spectrophotometer, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray diffraction (XRD). The construction of highly ordered nano and microstructures are operated by the property of π-conjugated dye molecules in more polar organic solvents due to π-π interaction between the perylene cores. From the UV–vis data, it is clear that the dye molecule shows solvatochromic behavior in low polar organic solvents and self-assembled behavior in methanol. The effect of bulky group at bay position and alkyl chain on imide position was investigated using UV–Vis absorption, differential scanning calorimetry (DSC), thermogravometric analysis (TGA), cyclic voltammetry (CV) and XRD. SEM and TEM images reveal the nano-architectonics morphology having diameter ≈400 ?nm. The d spacing values of XRD pattern has conformed π-π interactions. The effect of triphenylamine substituents on the π-π interaction between perylene molecules, the morphology of nano-architectonics and absorption properties of compound 1 are investigated by DFT calculations. On the basis of molecular orbitals, we have explained the electronic transitions and energy state in compound 1. The conjugation in compound 1 is affected by the degree of twisting in perylene ring due to the substituent at the bay positions of the perylene core.
