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  • 4,7-Dibromo-2,1,3-benzothiadiazole CAS 15155-41-6 4,7-Dibromobenzo[c][1,2,5]thiadiazole CAS no 15155-41-6 2,1,3-Benzothiadiazole,4,7-dibromo-

    Cas No: 15155-41-6

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15155-41-6 Usage

Description

4,7-Dibromo-2,1,3-benzothiadiazole is the building block or monomer for organic semiconductors synthesis in the application of light-emitting diodes and photovoltaic devices. Intermediate for the synthesis of i.e. PCDTBT and PCPDTBT.

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 15155-41-6 differently. You can refer to the following data:
1. 4,7-Dibromo-2,1,3-benzothiadiazole is the building block or monomer for the synthesis of light-emitting diodes and conducting polymers for organic electronics. It is used as an intermediate for the synthesis of poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) and poly[2,1,3-benzothiadiazole-4,7-diyl[4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl]] (PCPDTBT).
2. This monomer is used in the synthesis of photoactive acceptor part in low band gap conjugated polymers and oligomers for high performance OPV devices

Check Digit Verification of cas no

The CAS Registry Mumber 15155-41-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,1,5 and 5 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 15155-41:
(7*1)+(6*5)+(5*1)+(4*5)+(3*5)+(2*4)+(1*1)=86
86 % 10 = 6
So 15155-41-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H2Br2N2S/c7-3-1-2-4(8)6-5(3)9-11-10-6/h1-2H

15155-41-6 Well-known Company Product Price

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  • TCI America

  • (D3842)  4,7-Dibromo-2,1,3-benzothiadiazole  >98.0%(GC)

  • 15155-41-6

  • 1g

  • 180.00CNY

  • Detail
  • TCI America

  • (D3842)  4,7-Dibromo-2,1,3-benzothiadiazole  >98.0%(GC)

  • 15155-41-6

  • 5g

  • 780.00CNY

  • Detail
  • TCI America

  • (D3842)  4,7-Dibromo-2,1,3-benzothiadiazole  >98.0%(GC)

  • 15155-41-6

  • 25g

  • 2,800.00CNY

  • Detail
  • Alfa Aesar

  • (H56306)  4,7-Dibromo-2,1,3-benzothiadiazole, 97%   

  • 15155-41-6

  • 5g

  • 566.0CNY

  • Detail
  • Alfa Aesar

  • (H56306)  4,7-Dibromo-2,1,3-benzothiadiazole, 97%   

  • 15155-41-6

  • 25g

  • 1877.0CNY

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  • Aldrich

  • (693847)  4,7-Dibromobenzo[c]-1,2,5-thiadiazole  95%

  • 15155-41-6

  • 693847-1G

  • 460.98CNY

  • Detail
  • Aldrich

  • (693847)  4,7-Dibromobenzo[c]-1,2,5-thiadiazole  95%

  • 15155-41-6

  • 693847-5G

  • 1,634.49CNY

  • Detail
  • Aldrich

  • (778109)  4,7-Dibromobenzo[c]-1,2,5-thiadiazole  99.5% (GC)

  • 15155-41-6

  • 778109-1G

  • 1,641.51CNY

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15155-41-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE

1.2 Other means of identification

Product number -
Other names 4,7-Dibromobenzo[c]-1,2,5-thiadiazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

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More Details:15155-41-6 SDS

15155-41-6Relevant articles and documents

Novel 2,1,3-benzothiadiazole derivatives used as selective fluorescent and colorimetric sensors for fluoride ion

Wu, Jiefei,Lai, Guoqiao,Li, Zhifang,Lu, Yunxiang,Leng, Taohua,Shen, Yongjia,Wang, Chengyun

, p. 268 - 276 (2016)

Two novel 2,1,3-benzothiadiazole derivatives, used as colorimetric and fluorescent sensors for fluoride ion were designed, synthesized and characterized. These sensors contained single hydrogen-bond functional groups, which acted as interacting sites for fluoride ion. Both sensors displayed a red color in dimethyl sulfoxide solution. Binding studies revealed that they showed noticeable colorimetric and fluorescent responses only to F- among the eight anions tested (F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and NO3-). 1H NMR titration proved that the interaction between compounds and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Moreover, those compounds showed high sensitivity and selectivity for fluoride ion by inhibiting the excited state intramolecular proton transfer processes, and the detective processes could be followed by direct visual observation.

2,3-di(2-furyl) quinoxaline bearing 3 -ethyl rhodanine and 1,3 indandione based heteroaromatic conjugated T-shaped push -pull chromophores: Design, synthesis, photophysical and non-linear optical investigations

Gopi, Vidya,Subbiahraj, Saravanan,Chemmanghattu, Karthika,Ramamurthy, Praveen C.

, (2020)

The design, synthesis, computational, spectroscopic, and, the second and third order non-linear optical studies of a two new π-deficient cross-conjugated T-shaped push-pull molecules (QFR and QFI) consisting of 3-ethyl rhodanine and 1,3 indandione substit

Deep-red electroluminescent polymers: Synthesis and characterization of new low-band-gap conjugated copolymers for light-emitting diodes and photovoltaic devices

Yang, Renqiang,Tian, Renyu,Yan, Jingai,Zhang, Yong,Yang, Jian,Hou, Qiong,Yang, Wei,Zhang, Chi,Cao, Yong

, p. 244 - 253 (2005)

A novel series of semiconducting conjugated copolymers, derived from alkyl-substituted fluorene, 4,7-diselenophen-2′-yl-2,1,3-benzothiadiazole (SeBT), and 4,7-diselenophen-2′-yl-2,1,3-benzoselenadiazole (SeBSe), was synthesized by a palladium-catalyzed Su

Donor-acceptor-integrated conjugated polymers based on carbazole[3,4-c:5,6- c]bis[1,2,5]thiadiazole with tight π-π Stacking for photovoltaics

Zha, Daijun,Chen, Lie,Wu, Feiyan,Wang, Hongming,Chen, Yiwang

, p. 565 - 574 (2013)

An original strategy to construct a new donor-acceptor (D-A)-integrated structure by directly imposing "pull" unit on the "push" moiety to form fused ring architecture has been developed, and poly{N-alkyl-carbazole[3,4-c:5,6-c]bis[1,2,5]thiadiazole-alt-thiophene} (PCBTT) with D-A-integrated structure, in which two 1,2,5-thiadiazole rings are fixed on carbazole in 3-, 4- and 5-, 6-position symmetrically and thiophene is used as bridge, has been synthesized. The interaction between pull and push units has fine tuned the HOMO/LUMO energy levels, and the resulting copolymer covers the solar flux from 300 to 750 nm. The interaction between pull and push units is worth noting that due to the fused five rings inducing strong intermolecular interaction, an extremely short π-π stacking distance of 0.32 nm has been achieved for PCBTT both in powder and solid states. This is the shortest π-π stacking distance reported for conjugated polymers. Additionally, an obvious intramolecular charge transfer and energy transfer from donor units to acceptor units have been detected in this D-A integration. A moderate-to-high open-circuit voltage of ~0.7 V in PCBTT:[6,6]-phenyl-C61 butyric acid methyl ester (PCBM) (w/w = 1/2) solar cells is achieved due to the low-lying HOMO energy level of PCBTT.

Photophysical and photovoltaic properties of truxene-functionalized conjugated polymer-fullerene supramolecular complexes

Wen, Hua-Wen,Yang, Po-Chih

, p. 60308 - 60317 (2016)

We report the synthesis, characterization, and photophysical and photovoltaic properties of two truxene-functionalized conjugated copolymers (P1 and P2) containing various 2,1,3-benzothiadiazole segments; P1 and P2 were synthesized using Suzuki and Heck c

Design and development of dithienopyrrolobenzothiadiazole (DTPBT)-based rigid conjugated polymers with improved hole mobilities

Bhanvadia, Viraj J.,Machhi, Hiren K.,Soni, Saurabh S.,Zade, Sanjio S.,Patel, Arun L.

, (2020)

Donor-acceptor integrated ladder-type dithienopyrrolobenzothiadiazole (DTPBT)-based conjugated building blocks have been used to develop rigid conjugated polymers by copolymerizing them with synthesized ladder-type indoloquinoxaline, π-extended isoindigo and π-extended 2,1,3-benzothiadiazole-based conjugated building blocks. Structural aspects of synthesized building blocks are studied by single-crystal X-ray diffraction, which revealed the co-planar structure of indoloquinoxaline-scaffold while twisted but intramolecularly hydrogen-bonded structures of π-extended isoindigo- and 2,1,3-benzothiadiazole-scaffolds with number of intermolecular non-bonding interactions. The synthesized DTPBT-based conjugated polymers P-1, P-2 and P-3 are studied for photophysical and electrochemical properties and are found to have moderate to good visible light absorptivity with HOMO energy levels below ?5.0 eV. The X-ray diffraction studies indicate strong π?π stacking interactions induced face-on arrangement of polymer chains respective to the substrate. Polymers show π?π stacks promoted high space-charge limited current (SCLC) hole mobilities ranging between 5.6 × 10?4 –1.3 × 10?3 cm2V?1s?1. The obtained SCLC hole mobility data in tandem with the studied structural aspects of monomers and morphological aspects of polymers, suggest that the combination of ladder-type DTPBT-scaffolds (capable of intermolecular π?π interactions) with non-ladder-type planar and structurally rigid π-extended conjugated scaffolds (capable of intermolecular π?π and other non-bonding interactions) is beneficial for getting good hole mobilities.

Thiadiazole quinoxaline-based copolymers with ~1.0 eV bandgap for ternary polymer solar cells

Yu, Jiangsheng,An, Qiaoshi,Hai, Jiefeng,Nie, Xuemei,Zhou, Baojing,Zhang, Fujun,Tang, Weihua

, p. 12 - 20 (2015)

A new strong electron-deficient acceptor unit, 4,9-bis(5-bromothiophen-2-yl)-6,7-bis(5-dodecylthiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQxT), is designed. Three TQxT based new conjugated polymers have been further developed by alternating with benzo[1,2-b:4,5-b′]dithiophene or naphtho[1,2-b:5,6-b′]difuran. Featuring ultra low bandgaps of 1.03-1.10 eV, these polymers exhibit absorption spectra beyond near-infrared (NIR) region. The polymer:PC71BM (1:2) solar cells deliver a best power conversion efficiency (PCE) of 0.43%. The doping of 9 wt% PBDTT-TQxP into P3HT:PC71BM (1:2) blend, however, leads to a highest PCE of 3.58% for the resultant ternary solar cells, corresponding to ~22% improvement in comparison to 2.93% PCE for P3HT:PC71BM binary cells.

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Ams, Mark R.,Trapp, Nils,Schwab, Anatol,Mili?, Jovana V.,Diederich, Fran?ois

, p. 323 - 333 (2019)

Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3-benzothiadiazole X-ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S–2N CB square, halogen bonding (XB), S???S, and hydrogen-bonding (HB). A geometric model is employed to characterize the 2S–2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction.

A simple fluorene core-based non-fullerene acceptor for high performance organic solar cells

Suman,Bagui, Anirban,Datt, Ram,Gupta, Vinay,Singh, Surya Prakash

, p. 12790 - 12793 (2017)

A small molecule non-fullerene acceptor based on a fluorene core having a furan π-spacer and end capped with rhodanine (FRd2) is developed for solution processable bulk heterojunction organic solar cells (OSCs). The simplistic synthetic protocol reduces several reaction steps and hence production cost. Extended π-conjugation via furan units and the presence of electronegative rhodanine groups result in a power conversion efficiency of 9.4% in OSCs, which is the highest so far among these categories of molecules.

A non-fullerene acceptor with all "a" units realizing high open-circuit voltage solution-processed organic photovoltaics

Chen, Lingcheng,Huang, Linquan,Yang, Dong,Ma, Shuying,Zhou, Xin,Zhang, Jian,Tu, Guoli,Li, Can

, p. 2657 - 2662 (2014)

A novel non-fullerene small molecule electron acceptor TTzBT-DCAO, which contains all electron-withdrawing units of 2,1,3-benzothiadiazole, oligothiazole and alkyl cyanoacetate, has been synthesized and characterized. Its photophysical, electrochemical, and photovoltaic properties have been investigated. The material has favorable HOMO and LUMO levels of -5.88 and -3.60 eV, and shows strong absorption in the visible spectrum up to 650 nm. The small molecule:non-fullerene bulk-heterojunction organic photovoltaics (OPVs) were constructed based on two small molecules SF8TBT and TTzBT-DCAO. The influence of the donor:acceptor composition on device performance was investigated. The open-circuit voltages of the devices are over 1.20 V, which is among the highest values reported for single-junction OPVs. The results indicate that small molecules with all electron-withdrawing units could provide a novel route to efficient solution-processed OPVs with high open-circuit voltages.

Synthesis of bistriphenylamine- and benzodithiophene-based random conjugated polymers for organic photovoltaic applications

Cetin, Asli,Istanbulluoglu, Cagla,Hacioglu, Serife Ozdemir,Cevher, Sevki Can,Toppare, Levent,Cirpan, Ali

, p. 3705 - 3715 (2017)

In this study, donor–acceptor random polymers containing benzotriazole acceptor and bistriphenylamine and benzodithiophene donors, P1 and P2, were successfully synthesized by Stille coupling polymerization. The effect of bistriphenylamine moiety and thiophene π-conjugated linker on electrochemical, spectroelectrochemical, and optical behaviors of the polymers were investigated. Optoelectronic properties and photovoltaic performance of the polymers were examined under the illumination of AM 1.5G, 100 mW?cm?2. The polymers were characterized by cyclic voltammetry, UV-Vis-NIR absorption spectroscopy, gel permeation chromatography. HOMO/LUMO energy levels of P1 and P2 were calculated as ?5.47 eV/–3.41 eV and ?5.43 eV/–3.27 eV, respectively. Bulk heterojunction type solar cells were constructed using blends of the polymers (donor) and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) (acceptor). Photovoltaic studies showed that the highest power conversion efficiency of these photovoltaic devices were recorded as 3.50% with open circuit voltage; 0.79 V, short circuit current; 9.45 mA?cm?2, fill factor; 0.53 for P1:PC71BM (1:2, w/w) in 3% o-dichlorobenzene (o-DCB) solution and 3.15% with open circuit voltage; 0.75 V, short circuit current; 8.59 mA?cm?2, fill factor; 0.49 for P2:PC71BM (1:2, w/w) in 2% chlorobenzene (CB) solution.

Small band gap D-π-A-π-D benzothiadiazole derivatives with low-lying HOMO levels as potential donors for applications in organic photovoltaics: A combined experimental and theoretical investigation

Paramasivam, Mahalingavelar,Gupta, Akhil,Raynor, Aaron M.,Bhosale, Sheshanth V.,Bhanuprakash,Jayathirtha Rao

, p. 35318 - 35331 (2014)

In an attempt to develop small organic molecules with potential applications as donors in organic photovoltaic (OPV) devices, we have synthesized and characterized four novel benzothiadiazole (A) core structured D-π-A-π-D dyes featuring carbazole and benzocarbazole as donors (D) and fluorene and thiophene as spacers (π). The effects of the π-spacer units and variations in donor strength on the photophysical, electrochemical and thermal properties of the molecules have been investigated in detail. The replacement of fluorene by thiophene as a π-spacer promotes planarity, resulting in a larger bathochromic absorption shift, enhanced emission profiles and an enhanced intramolecular charge transfer (ICT) transition. The introduction of the benzocarbazole unit creates a low-lying HOMO level, as inferred from cyclic voltammetry studies. All the dyes exhibit remarkable thermal robustness. Theoretical calculations have been carried out to understand the structure-property relationships of the synthesized materials. The results obtained from the characterization methods reveal that the dyes with thiophene π-spacers show better optoelectronic properties compared to their fluorene counterparts. Solution-processable bulk-heterojunction devices with a structure of ITO/PEDOT:PSS (38 nm)/active layer/Ca (20 nm)/Al (100 nm) were fabricated using the materials investigated in this study as donors and (6,6)-phenyl C 61-butyric acid methyl ester (PC61BM) as an acceptor. A power conversion efficiency of 1.62% for the molecule with thiophene as a spacer and carbazole as donor/PC61BM was achieved for the preliminary photovoltaic devices under simulated AM 1.5 illumination (100 mW cm -2).

Differently substituted benzothiadiazoles as charge-transporting emitters for fluorescent organic light-emitting diodes

Gudeika, Dalius,Miasojedovas, Arunas,Bezvikonnyi, Oleksandr,Volyniuk, Dmytro,Gruodis, Alytis,Jursenas, Saulius,Grazulevicius, Juozas V.

, p. 217 - 225 (2019)

Carbazolyl- and 1,2,3,4-tetrahydrocarbazolyl-substituted benzothiadiazoles were prepared by Pd-catalyzed Buchwald-Hartwig and Heck reactions. Photophysical, electrochemical, thermal, charge-transporting properties, and performance in organic light emitting diodes (OLEDs) of the derivatives with donor-π-acceptor-π-donor and donor-acceptor-donor structures are discussed. Photo- and electroluminescent properties of the studied compounds of carbazole and benzothiadiazole are very sensitive to their molecular structures. Their glass transition temperatures range from 145 to 191 °C. Investigation of photophysical properties revealed importance of intramolecular twisting on excited state deactivation. Emission of dilute solutions of the compounds in nonpolar solvents appears in the orange region with fluorescence quantum yields up to 0.6.4,7-(Di (1,2,3,4-tetrahydro)carbazolyl)-[2,1,3]-benzothiadiazole demonstrates phosphorescence and delayed fluorescence at room temperature. Solid-state ionization potentials of the materials range from 5.64 to 5.82 eV. The layer of 4,7-(di (tert-butyl)carbazolyl)-[2,1,3]-benzothiadiazole shows high hole drift mobility of 1.7 × 10?3 cm2/V·s at an electric field of 5.3 × 105 V/cm and relatively high electron drift mobility of 5.7 × 10?5 cm2/V·s at an electric field of 5.8 × 105 V/cm. Red OLEDs based of singlet emission with maximum external quantum efficiency values of 1.3 and 0.13% were achieved using new emitters. Much better electroluminescent performance was observed for the compound having donor-acceptor-donor structure relative to the compound with donor-π-acceptor-π-donor structure.

Benzothiadiazole-based D-π-A-π-D fluorophores: Synthesis, self-assembly, thermal and photophysical characterization

Fang, Haipeng,Gao, Hongfei,Wang, Tingyan,Zhang, Bei,Xing, Wei,Cheng, Xiaohong

, p. 190 - 198 (2017)

A symmetrical linear D-π-A-π-D hexacatenar compound with 2,1,3-benzothiadiazole as the acceptor core connected at its 4,7 position with phenylthienylethynyl spacers has been designed and synthesized. This compound displays liquid crystalline property with oblique columnar mesophase and forms an organogel in dichloromethane. The investigation of photophysical and electrochemical properties reveals that this compound can exhibit broad and strong absorption band at the range of 300–700 nm with a low energy gap in solid state, meanwhile it exhibits highly red fluorescent emission and large Stokes shifts.

Impact of the different electron-releasing subunits on the dye-sensitized solar cell performance of new triphenylamine-benzimidazole based molecules

Din?alp, Haluk,Saltan, G?zde Murat,Aykut, Deniz,Zafer, Ceylan

, p. 157 - 165 (2015)

New triphenylamine-benzimidazole type small molecules with different electron-releasing groups were designed and synthesized to investigate their photovoltaic performances in dye sensitized solar cells (DSSCs). Their good visible absorptions covering the 400-535 nm in addition to suitable lowest unoccupied molecular orbital (LUMO) energy levels between -3.03 and -3.11 eV make good candidates them for DSSC devices. Fluorescence quenching studies of the dyes with pristine titania support the good electron injection to conduction band of TiO2. Time resolved measurements of the dyes in solutions indicate the occurence of charge generation during the excited state. One of the used dyes in DSSC devices, TPA5a, carrying a methoxy group in triphenylamine part of the structure, gave much higher power conversion efficiency (PCE) value of 4.31% as compared to the other derivatives. Device fabricated from TPA5a dye gives good external quantum efficiency (EQE) value above 70% at 460 nm. Also, electron impedance spectroscopy (EIS) analysis of the devices gives a good explanation of the understanding of the cell performances.

Enhancing the power conversion efficiency of polymer solar cells: Via selection of quinoxaline substituents

Karaga?ti, ?zge,Cevher, Sevki Can,Hizalan, Gonul,Hacioglu, Serife O.,Toppare, Levent,Cirpan, Ali

, p. 14635 - 14645 (2017)

In this study, three random copolymers including quinoxaline derivatives with different substituent groups, 2,6-bis(trimethylstannyl)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene and 4,7-dibromo-2-(2-octyldodecyl)-2H-benzo[d][1,2,3]triazole, wer

Syntheses and photoluminescence properties of rhenium(I) complexes based on dipyrido[3,2-a:2',3'-c]phenazine derivatives with carbazole moiety

Zhou, Yong-Hui,Wang, Zheng-Mei,Chen, Min-Dong,Guo, Sheng-Li,Zheng, You-Xuan

, p. 958 - 965 (2013)

Four rhenium(I) complexes ReL1-ReL4 based on dipyrido[3,2-a:2',3'-c]phenazine (L1) and derivatives L 2-L4 ligands (L2: 10,13-dibromodipyrido[3,2-a:2',3'-c] phenazine, L3: 10-bromo-13-carbazolyl-dipyrido[3,2-a:2',3'-c] phenazine, L4: 10,13-dicarbazolyldipyrido[3,2-a:2',3'-c]phenazine) were synthesized and characterized. The Re(I) complexes ReL1-ReL4 show photoluminescent emissions at 556, 582, 637 and 662 nm, respectively, assigned to dp (Re)→p/ (diimine) MLCT phosphorescence in CH2CL 2 solution. The carbazole containing complexes ReL3 and ReL4, as compared to ReL1, exhibit higher luminescence. These observations imply that modification of diimine rhenium(I) carbonyl complexes with carbazole moiety would lead to efficient phosphorescent properties.

Star-Shaped Single-Polymer Systems with Simultaneous RGB Emission: Design, Synthesis, Saturated White Electroluminescence, and Amplified Spontaneous Emission

Liu, Cheng-Fang,Jiu, Yuanda,Wang, Jianyun,Yi, Jianpeng,Zhang, Xin-Wen,Lai, Wen-Yong,Huang, Wei

, p. 2549 - 2558 (2016)

A three-armed star-shaped single-polymer system comprising tris(4-(3-hexyl-5-(7-(4-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophen-2-yl)phenyl)amine (TN) as red emissive cores, benzothiadiazole (BT) as green emissive dopants, and polyfluorene (

Dithienosilole–phenylquinoxaline-based copolymers with A-D-A-D and A-D structures for polymer solar cells

Keshtov, Mukhamed L.,Khokhlov, Alexei R.,Kuklin, Sergei A.,Nikolaev, Alexander Yu,Koukaras, Emmanuel N.,Sharma, Ganesh D.

, p. 376 - 386 (2018)

Two copolymers having D-A-D-A (P1) and D-A (P2) structures with quinoxaline acceptor unit and dithienosilole donor unit were synthesized and their optical and electrochemical (both experimental and theoretical) properties were investigated. The optical pr

Fluorescence polymer incorporating triazole and Benzo[2,1,3]thiadiazole moieties for Ni2+ detection

Huang, Xiaobo,Dong, Yu,Meng, Jie,Cheng, Yixiang,Zhu, Chengjian

, p. 1841 - 1844 (2010)

Conjugated polymer could be obtained by the polymerization of 4,7-diethynylbenzo[2,1,3]thiadiazole (M-1) with 1,4-diazidobenzene (M-2) via click reaction. The polymer shows strong blue-green fluorescence due to the extended π-electronic structure in the m

High efficiency and low efficiency roll-off hole-transporting layer-free solution-processed fluorescent NIR-OLEDs based on oligothiophene-benzothiadiazole derivatives

Chaiwai, Chaiyon,Chasing, Pongsakorn,Kaewpuang, Terdkait,Manyum, Thanaporn,Namuangruk, Supawadee,Promarak, Vinich,Sudyoadsuk, Taweesak

, p. 5045 - 5050 (2020)

We report on simple low band-gap D-A-D type chromophores comprising triphylamine as a donor and oligothiophene-benzothiadiazoles as an acceptor. In the solid state, they exhibited strong near-infrared (NIR) emission with high fluorescence quantum yield wh

Synthesis and Characterization of Acid-Responsive Luminescent Fe(II) Metallopolymers of Rigid and Flexible Backbone N-Donor Multidentate Conjugated Ligands

Kumar, Anil,Bawa, Shubham,Ganorkar, Kapil,Ghosh, Sujit Kumar,Bandyopadhyay, Anasuya

, p. 1746 - 1757 (2020)

In this report we have disclosed the syntheses and properties of two new conjugated organic moieties bearing the same coordination sites but possessing different backbone rigidities and rotational flexibilities. Two new metallopolymers have been synthesized from the corresponding ligands under identical reaction conditions, and they have been thoroughly characterized through different techniques to understand the effect of backbone rigidity on the evolution of different properties in these metallopolymers. A FESEM micrograph of the rigid metallopolymer confirms the formation of a rigid nanorod type structure, while long agglomerated nanofiber strands are visible on the substrate in the case of the flexible analogue. All of the newly synthesized materials are fluorescence active. An Fe(II) metallopolymer of the flexible ligand showed huge changes in emission properties in the presence of different acids and showed a possibility of it being used as a thin film acid vapor sensor. All of the materials showed reversible electrochemical activity, and both of these polymers have shown electroluminescence when an appropriate potential is applied.

Photophysical and electrochemical properties of π-extended molecular 2,1,3-benzothiadiazoles

DaSilveira Neto, Brenno A.,Lopes, Aline Sant'Ana,Ebeling, Gunter,Gon?alves, Reinaldo S.,Costa, Valentim E. U.,Quina, Frank H.,Dupont, Jairton

, p. 10975 - 10982 (2005)

The reaction of 4,7-dibromo-2,1,3-benzothiadiazole with arylboronic acids (phenyl, 1-naphthyl, 4-methoxyphenyl, 4-chlorophenyl and 4- trifluoromethylphenyl) in the presence of catalytic amounts of a NCP-pincer palladacycle affords photoluminescent π-extended 4,7-diaryl-2,1,3- benzothiadiazoles 4a-e in high yields. These 4,7-diaryl-2,1,3-benzothiadiazoles exhibit high fluorescent quantum yields, high electron affinities and adequate band gap values for testing as OLEDs. The 4,7-bis-naphthyl-2,1,3- benzothiadiazole 4b presents two different lifetimes (bi-exponential decay) due to the presence of two atropisomers. The Sonogashira coupling reaction of 4,7-diethynyl-2,1,3-benzothiadiazole 6 with the corresponding halo-aryl compounds (iodobenzene, 1-bromonaphthalene, 4-iodoanisole, 4-bromo-N,N- dimethylaniline and 2-bromopyridine) afforded the photoluminescent π-extended 4,7-bis-alkynylaryl-2,1,3-benzothiadiazoles 7a-e, also in high yields. These 4,7-diethynyl-2,1,3-benzothiadiazoles also present high fluorescent quantum yields, high electron affinities and adequate band gap values for testing as OLEDs. The 4,7-disubstituted-2,1,3-benzothiadiazoles 4a-e and 7a-e exhibit different electrochemical behavior. The presence of two ethynyl spacers in 2,1,3-benzothiadiazoles 7a-e shifts the reduction potentials to less cathodic values and also results in two well-defined and distinct reduction processes.

Achieving yellow emission by varying the donor/acceptor units in rod-shaped fluorenyl-alkynyl based π-conjugated oligomers and their binuclear gold(i) alkynyl complexes

Islam, Sk Najmul,Sil, Amit,Patra, Sanjib K.

, p. 5918 - 5929 (2017)

Fluorenyl-alkynyl based π-conjugated rod-shaped oligomers bearing different central aromatic moieties and functionalizable di-alkynyl termini, such as H - Fl - Fl - Fl - H (OH1), H - Fl - Btz - Fl - H (OH2) and H - Fl - Btd - Fl - H (OH3) where Fl = 9,9-d

Fluorescence emission enhancement of a T-shaped benzimidazole with a mechanically-interlocked ‘suit’

Xu, Houyang,Lin, Meng-Di,Yuan, Jun,Zhou, Baiyang,Mu, Yingxiao,Huo, Yanping,Zhu, Kelong

supporting information, p. 3239 - 3242 (2021/04/06)

A fluorescent T-shaped benzimidazole was successfully designed and interlocked in a bicyclic macrocycle to form a suit[1]ane through supramolecular templated-synthesis. Compared with the bare fluorophore, suit[1]ane requires nearly two times the concentration to initialize the aggregation-caused quenching effect in solution. Furthermore, an 8-fold higher solid-state fluorescence quantum yield (21.7%) is also achieved. By taking advantage of mechanical bonding and molecular packing, such fluorescence emission enhancement through formation of a suitane opens the way to new complex fluorescent materials.

Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications

Aslan, Sultan Taskaya,Cevher, Duygu,Bolay?r, Eda,Hizalan Ozsoy, Gonul,Arslan Udum, Yasemin,Y?ld?r?m, Erol,Toppare, Levent,Cirpan, Ali

, (2021/10/05)

A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.

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