32281-36-0Relevant articles and documents
"roller-Wheel"-Type Pt-Containing Small Molecules and the Impact of "rollers" on Material Crystallinity, Electronic Properties, and Solar Cell Performance
He, Wenhan,Livshits, Maksim Y.,Dickie, Diane A.,Zhang, Zhen,Mejiaortega, Luis E.,Rack, Jeffrey J.,Wu, Qin,Qin, Yang
, p. 14109 - 14119 (2017)
We report the synthesis, characterization, and detailed comparison of a series of novel Pt-bisacetylide containing conjugated small molecules possessing an unconventional "roller-wheel" shaped structure that is distinctly different from the "dumbbell" designs in traditional Pt-bisacetylide containing conjugated polymers and small molecules. The relationships between the chemical nature and length of the "rollers" and the electronic and physical properties of the materials are carefully studied by steady-state spectroscopy, cyclic voltammetry, differential scanning calorimetry, single-crystal X-ray diffraction, transient absorption spectroscopy, theoretical calculation, and device application. It was revealed that if the roller are long enough, these molecules can "slip-stack" in the solid state, leading to high crystallinity and charge mobility. Organic solar cells were fabricated and showed power conversion efficiencies up to 5.9%, out-performing all existing Pt-containing materials. The device performance was also found to be sensitive to optimization conditions and blend morphologies, which are a result of the intricate interplay among materials crystallinity, phase separation, and the relative positions of the lowest singlet and triplet excited states.
A Facile Synthesized Polymer Featuring B-N Covalent Bond and Small Singlet-Triplet Gap for High-Performance Organic Solar Cells
Pang, Shuting,Wang, Zhiqiang,Yuan, Xiyue,Pan, Langheng,Deng, Wanyuan,Tang, Haoran,Wu, Hongbin,Chen, Shanshan,Duan, Chunhui,Huang, Fei,Cao, Yong
supporting information, p. 8813 - 8817 (2021/03/16)
High-efficiency organic solar cells (OSCs) largely rely on polymer donors. Herein, we report a new building block BNT and a relevant polymer PBNT-BDD featuring B-N covalent bond for application in OSCs. The BNT unit is synthesized in only 3 steps, leading to the facile synthesis of PBNT-BDD. When blended with a nonfullerene acceptor Y6-BO, PBNT-BDD afforded a power conversion efficiency (PCE) of 16.1 % in an OSC, comparable to the benzo[1,2-b:4,5-b′]dithiophene (BDT)-based counterpart. The nonradiative recombination energy loss of 0.19 eV was afforded by PBNT-BDD. PBNT-BDD also exhibited weak crystallinity and appropriate miscibility with Y6-BO, benefitting of morphological stability. The singlet–triplet gap (ΔEST) of PBNT-BDD is as low as 0.15 eV, which is much lower than those of common organic semiconductors (≥0.6 eV). As a result, the triplet state of PBNT-BDD is higher than the charge transfer (CT) state, which would suppress the recombination via triplet state effectively.
Effect of fluorine on optoelectronic properties in DI-A-DII-A-DI type organic molecules: A combined experimental and DFT study
Appalanaidu, Ejjurothu,Busireddy, Manohar Reddy,Chetti, Prabhakar,Vaidya, Jayathirtha Rao,Vidya, V. M.
, (2020/03/17)
The impact of the substitution of fluorine atom/atoms on the optoelectronic features of organic molecules having DI-A-DII-A-DI type architecture is examined in the current work. The three synthesized organic molecules (SMD1, SMD2 and SMD3) comprise of a dithienopyrrole (DTP) derivative as a central donor (DII), which is flanked between two benzothiadiazole (BT) moieties (electron acceptors, A). The BT core on each of two ends is joined to an electron-donating benzodithiophene (BDT) derivative (DI). The SMD1, SMD2 and SMD3 are substituted with 0, 2 and 4 fluorine atoms on their BT moiety respectively. The assistance of DFT methods is taken to evaluate the influence of fluorine on reorganization energies, ionizing potential and electron affinity of molecules. The thermal stability of molecules is mapped by TGA studies. Cyclic voltammetry studies are carried out to comprehend the characteristics of highest molecular orbital, lowest unoccupied molecular orbital and the bandgap of molecules, which are also supported by DFT methods. The molecules displayed better absorption properties in the near-infrared (NIR) region, excellent solution processability in a variety of organic solvents, low bandgap and optimum thermal toughness to make them applicable in the construction of OBHJSCs to play the role of donor materials when connected with acceptors like fullerene derivatives.
Regioisomeric BODIPY Benzodithiophene Dyads and Triads with Tunable Red Emission as Ratiometric Temperature and Viscosity Sensors
Aswathy,Sharma, Sushil,Tripathi, Narendra Pratap,Sengupta, Sanchita
supporting information, p. 14870 - 14880 (2019/11/13)
Regioisomeric acceptor-donor (AD) molecular rotors (p-AD, m-AD and m-ADA) were synthesized and characterized, wherein dyads p-AD and m-AD, and triad m-ADA contained 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) and benzodithiophene (BDT) as electron-acceptor and electron-donor, respectively. In all the compounds, the donor and acceptor moieties are electronically decoupled by a phenyl spacer, either through a para coupling or through a meta coupling. The dyad counterparts p-AD and m-AD showed distinct photophysical characteristics in which dyad p-AD showed TICT band at ca. 654 nm characterized by a Stokes shift of ca. 150 nm and prominent solvatochromism. However, meta regioisomeric triad m-ADA showed well-defined aggregation in solution. Notably, because of the temperature-tunable and solvent-viscosity-dependent emission, efficient ratiometric temperature sensing with positive and negative temperature coefficients and viscosity sensing was observed for all compounds. Interestingly, the fluorescence of dyad m-AD (in 10/90 v/v THF/water) revealed a near-white light emission with CIE chromaticity coordinates (x, y) of (0.32, 0.29). Furthermore, the fluorescence emission of p-AD in THF at 0 °C also showed a near-white light emission with chromaticity coordinates (x, y) of (0.34, 0.27). Such multifunctional rotors with readily tunable emission in the red region and prominent temperature- and viscosity-sensing abilities are promising for sensing and bioimaging applications.
High-efficiency synthetic method of 2,6-dibromobenzo[1,2-B:4,5-B]dithiophenol-4,8-diketone
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Paragraph 0022; 0024; 0025; 0026; 0034; 0038; 0040; 0041-042, (2017/07/20)
The invention discloses a high-efficiency synthetic method of 2,6-dibromobenzo[1,2-B:4,5-B]dithiophenol-4,8-diketone. The high-efficiency synthetic method comprises the following steps: (1) synthesizing benzo[1,2-B:4,5-B]dithiolphenol-4,8-diketone; and (2) performing bromination reaction for the benzo[1,2-B:4,5-B]dithiolphenol-4,8-diketone. By adopting the high-efficiency synthetic method of 2,6-dibromobenzo[1,2-B:4,5-B]dithiophenol-4,8-diketone, the yield of the product 2,6-dibromobenzo[1,2-B:4,5-B]dithiophenol-4,8-diketone is greatly increased, and the requirement on the atom economy can be realized.
Dithieno[3,2-b:2′,3′-d]pyrrole-benzo[c][1,2,5]thiadiazole conjugate small molecule donors: Effect of fluorine content on their photovoltaic properties
Busireddy, Manohar Reddy,Chereddy, Narendra Reddy,Shanigaram, Balaiah,Kotamarthi, Bhanuprakash,Biswas, Subhayan,Sharma, Ganesh Datt,Vaidya, Jayathirtha Rao
, p. 20513 - 20522 (2017/08/26)
Two new small molecule donors, namely ICT4 and ICT6 with D1-A-D2-A-D1 architecture having 2,4-bis(2-ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole (EHDTP, D1) and 4,8-bis((2-ethylhexyl)oxy)benzo[1,2-b:4,5-b′]dithiophene (OBDT, D2) as the terminal and central donor, and benzo[c][1,2,5]thiadiazole (BT for ICT4) and 5,6-difluorobenzo[c][1,2,5]thiadiazole (F2BT for ICT6) as the acceptor (A) moieties, are synthesized and their optical, electronic and photovoltaic properties are investigated. Both ICT4 and ICT6 have considerable solubility in various solvents and possess efficient light absorption ability [ε (×105 mol-1 cm-1) is 0.99 and 1.06, respectively for ICT4 and ICT6] and appropriate frontier molecular orbital energy offsets with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM). Bulk heterojunction solar cells (BHJSCs) are fabricated using ICT4/ICT6 and PC71BM as donors and acceptors, respectively and BHJSCs with two-step annealed (thermal followed by solvent vapor annealing) active layers of ICT4 and ICT6 show overall power conversion efficiencies (PCEs) of 5.46% and 7.91%, respectively. The superior photovoltaic performance of the ICT6 based BHJSCs is due to the favourable morphology with a nanoscale interpenetrating network in the ICT6:PC71BM active layer induced by the fluorine atoms on the BT acceptor, which significantly enhances the dissociation of excitons, charge transport and the charge collection efficiency, and suppresses bimolecular recombination in the BHJ. The observed higher PCE of 7.91% indicates that ICT6 is one of the best BT based donor material for small molecular BHJSCs.
C10H4O2S2/graphene composite as a cathode material for sodium-ion batteries
Chen, Xiaoju,Wu, Yiwen,Huang, Zhongkang,Yang, Xiaoyun,Li, Weijie,Yu, Laura Chuan,Zeng, Ronghua,Luo, Yifan,Chou, Shu-Lei
, p. 18409 - 18415 (2016/12/07)
Organic electroactive materials are promising candidates for next generation sodium ion batteries (SIBs) due to their low cost, sustainability and environmental benignity. It is of great interest to develop organic compounds with multifunctional groups to be used as electrode materials for SIBs owing to their light weight, multi-electron reactions, redox stability and structural diversity. The organic compound 4,8-dihydrobenzo[1,2-b:4,5-b′] dithiophene-4,8-dione (BDT) was prepared by a facile solution method, and its graphene composite (BDT-G) was synthesized by a simple dispersion-deposition process. BDT-G as a cathode material demonstrated much enhanced electrochemical performance, including higher reversible capacity (217 mA h g-1vs. 145 mA h g-1), better cycling performance (～175 mA h g-1vs. ～100 mA h g-1 after 70 cycles at 0.2C), and higher rate capabilities (1.7 times better than BDT at 2C) compared with BDT. It is revealed that these improved electrochemical properties should be mainly attributed to the excellent electronic conductivity and ionic transport efficiency promoted by graphene. Furthermore, the fast electrode reaction of BDT with the help of unlimited electron transport via the two-dimensional graphene network results in enhanced usage of materials, and BDT in the composite with graphene could be inhibited from dissolution in the organic electrolyte.
Dithienopyrrole-benzodithiophene based donor materials for small molecular BHJSCs: Impact of side chain and annealing treatment on their photovoltaic properties
Busireddy, Manohar Reddy,Mantena, Venkata Niladri Raju,Chereddy, Narendra Reddy,Shanigaram, Balaiah,Kotamarthi, Bhanuprakash,Biswas, Subhayan,Sharma, Ganesh Datt,Vaidya, Jayathirtha Rao
, p. 312 - 325 (2016/07/21)
Two small molecular organic materials denoted as ICT1 and ICT2 with A-D1-D2-D1-A architecture have been synthesized and their thermal, photo-physical, electrochemical and photovoltaic properties are explored. Synthesized materials have n-butylrhodanine acceptor (A), dithienopyrrole (DTP) (D1) and benzodithiophene (BDT) (D2) (Alkoxy BDT and alkylthiophene BDT, respectively for ICT1 and ICT2) donor moieties. Both the materials have good solubility (up to 25 mg/mL) in most common organic solvents and have excellent thermal stability with the decomposition temperature (Td) as 348 and 382 °C, respectively for ICT1 and ICT2. Both ICT1 and ICT2 have broad and intense visible region absorption (molar excitation coefficient is 1.71 × 105 and 1.65 × 105 mol?1 cm?1, respectively for ICT1 and ICT2) and have suitable HOMO and LUMO energy levels for PC71BM acceptor. Bulk heterojunction solar cells with ITO/PEDOT:PSS/blend/Al structure are fabricated using these materials. The BHJSCs fabricated by spin cast of ICT1:PC71BM and ICT2:PC71BM (1:2 wt ratio) blend from chloroform showed power conversion efficiency (PCE) of 2.77% (Jsc = 6.84 mA/cm2, Voc = 0.92 V and FF = 0.44) and 3.27% (Jsc = 7.26 mA/cm2, Voc = 0.96 V and FF = 0.47), respectively. Annealing the active layer significantly improved the PCE of these BHJSCs to 5.12% (Jsc = 10.15 mA/cm2, Voc = 0.87 V and FF = 0.58) and 5.90% (Jsc = 10.68 mA/cm2, Voc = 0.92 V and FF = 0.60), respectively for ICT1 and ICT2 donors. The enhancement in the PCE is due to higher light harvesting ability of the active layer, better nanoscale morphology for efficient and balanced charge transport and effective exciton dissociation at the donor-acceptor interface.
A highly selective and sensitive probe based on benzo[1,2-b:4,5-b′]dithiophene: Synthesis, detection for Cu(II) and self-assembly
Ma, Yuwen,Leng, Taohua,Lai, Guoqiao,Li, Zhifang,Xu, Xiaojia,Zou, Jianwei,Shen, Yongjia,Wang, Chengyun
, p. 2219 - 2225 (2016/04/09)
A novel turn-off probe for copper(II) containing benzo[1,2-b:4,5-b′]dithiophene (BDT) and two picolinamide units was synthesized. In this probe, two picolinamide units complex with one Cu2+ ion and two nitrogen atoms in each picolinamide unit coordinate with Cu2+, which is verified by DFT calculation. Its fluorescence quantum yield is 0.43 and the detection limit is as low as 2.4×10-8 mol/L. The results show that the probe displays good selectivity for Cu2+ over other ions (Mn2+, Pb2+, Cr3+, Zn2+, Ni2+, K+, Ca2+, Ag+, Mg2+, Fe3+, Fe2+, Hg2+, Al3+, Cd2+, Pd2+, Co2+). Furthermore, the probe induced by Cu2+ and the π-π interaction of the aromatic unit can also form rod structure assembly, which can be observed by scanning electron microscopy (SEM).
A Benzodithiophene-Based Fluorescence Probe for Rapid Detection of Fluoride Ion
Tan, Wenbin,Leng, Taohua,Lai, Guoqiao,Li, Zhifang,Wu, Jiefei,Shen, Yongjia,Wang, Chengyun
supporting information, p. 809 - 813 (2016/08/31)
A novel and simple fluorescence probe was synthesized from benzo[1,2-b:4,5-b′]dithiophene (BDT) and trimethylsilylethyne via Sonogashira reaction, and showed highly selective and sensitive fluorescence decreasing response towards F?. The probe molecule turned to a weakly fluorescent terminal alkyne moiety because its trimethylsilyl (TMS) group was cleaved by fluoride, which was proved by1H NMR titration. Whereas no distinct fluorescent changes were observed with the addition of other anions, such as Cl?, Br?, I?, AcO?and H2PO4?. Upon the addition of F?, the maximum fluorescence emission wavelength shifted from 460 nm to 450 nm with a decrease of fluorescence intensity by 40% within 20 s. Moreover, the detection limit towards F?was calculated to be as low as 73.5 nmol/L.
