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1000623-95-9

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  • Factory Price OLED 99% 1000623-95-9 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl) pyrrolo[3,4-c] pyrrole-1,4-dione Manufacturer

    Cas No: 1000623-95-9

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  • 3,6-Bis-(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)-pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

    Cas No: 1000623-95-9

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Description

3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP-EH-2ThBr) is a building block containing a?DPP backbone as a strong acceptor unit. It has a planar conjugated bi-cyclic structure engaging stronger π–π interactions. Due to its electron-deficient nature,?DPP-EH-2ThBr and its derivatives are used for the synthesis of small molecules and low band-gap polymer semiconductors?with OPV, OLED and perovskite solar cells.

Uses

suzuki reaction

Check Digit Verification of cas no

The CAS Registry Mumber 1000623-95-9 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,0,0,6,2 and 3 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1000623-95:
(9*1)+(8*0)+(7*0)+(6*0)+(5*6)+(4*2)+(3*3)+(2*9)+(1*5)=79
79 % 10 = 9
So 1000623-95-9 is a valid CAS Registry Number.
InChI:InChI=1S/C30H38Br2N2O2S2/c1-5-9-11-19(7-3)17-33-27(21-13-15-23(31)37-21)25-26(29(33)35)28(22-14-16-24(32)38-22)34(30(25)36)18-20(8-4)12-10-6-2/h13-16,19-20H,5-12,17-18H2,1-4H3

1000623-95-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-bis(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-3,6-dione

1.2 Other means of identification

Product number -
Other names K0106

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:1000623-95-9 SDS

1000623-95-9Relevant articles and documents

Synthesis and Spectroscopic Investigation of Diketopyrrolopyrrole - Spiropyran Dyad for Fluorescent Switch Application

Doddi, Siva,Narayanaswamy,Ramakrishna, Bheerappagari,Singh, Surya Prakash,Bangal, Prakriti Ranjan

, p. 1939 - 1949 (2016)

We report the synthesis and characterization of a new fluorescent dyad SP-DPP-SP(9) via efficient palladium-catalyzed Sonogashira coupling of prop-2-yn-1-yl 3-(3′,3’dimethyl-6-nitrospiro[chromene-2,2′-indolin]-1′-yl)propanoatespiropyran, SP(8), a well known photochromic accepter, with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis((R)-2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, DPP(4), a highly fluorescent donor. Under visible light exposure the SP unit is in a closed hydrophobic form, whereas under UV irradiation it converts to a polar, hydrophilic open form named Merocyanine (MC), which is responsible for functioning of photo-switch application. The photochemistry pertaining to fluorescence switch, ‘on/off’ behaviour, of model dyad SP-DPP-SP(9) is experimentally analyzed in solution as well as in solid state in polymer matrices by photoluminescence(PL) and absorption spectroscopy. After absorption of UV light the spiropyran unit of the dyad under goes the rupture of the spiro C-O bond leading to the formation of MC. The absorption band of MC fairly overlaps to the fluorescence of DPP unit resulting quenching of fluorescence via fluorescence resonance energy transfer from exited DPP unit to ground state MC. In contrary, the fluorescence of DPP is fully regained upon transformation of MC to SP by exposure to visible light or thermal stimuli. Hence, the fluorescence intensity of dyad 9 is regulated by reversible conversion among the two states of the photochromic spiropyran units and the fluorescence resonance energy transfer (FRET) between the MC form of SP and the DPP unit. Conversely, these scrutiny of the experiment express that the design of dyad 9 is viable as efficient fluorescent switch molecule in many probable commercial applications, such as, logic gates and photonic and optical communications.

Air-stable ambipolar organic field-effect transistors based on naphthalenediimide-diketopyrrolopyrrole copolymers

Wang, Ping,Li, Hui,Gu, Chunling,Dong, Huanli,Xu, Zhenzhen,Fu, Hongbing

, p. 19520 - 19527 (2015)

Two air-stable polymeric semiconductors were rationally designed and synthesized, namely PNDI-DPP and PNDI-T(DPP)T, containing naphthalenediimide (NDI) units and diketopyrrolopyrrole (DPP). The coplanar thiophene-substituted DPP moieties act as donors rather than acceptors, even though DPP is an electron-deficient core. In a bottom-gate/top-contact device architecture, the effect of changing the number of thiophene linkers on the performance of the two completely different OFETs was investigated. PNDI-T(DPP)T presented unipolar p-type behaviour with an average hole mobility of 0.02 cm2 V-1 s-1, while PNDI-DPP exhibited ambipolar transport with average electron and hole mobilities of 5.7 × 10-3 and 1.6 × 10-3 cm2 V-1 s-1, respectively. Moreover, OFETs based on the two polymers showed good air-stability with negligible changes after being stored under ambient conditions for over 3 months. This journal is

Synthesis and properties of Zn2+/Cd2+-directed self-assembled metallo-supramolecular polymers based on 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) derivatives

Chen, Xuegang,Guo, Kai,Li, Fanchao,Zhou, Li,Qiao, Hongbin

, p. 58027 - 58035 (2014)

New building blocks based on 1,4-diketopyrrolo[3,4-c]pyrrole (DPP), 2,5-bis(2-ethylhexyl)-3,6-bis(5-[p-(2,2':6′,2′′-terpyridine-4′-yl) phenyl]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M1) and 2,5-bis(2-ethylhexyl)-3,6-bis(4-[p-(2,2′:6′,2′′-terpyridine-4′-yl) phenyl]phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M2) were synthesized by the Suzuki Pd-catalyzed cross-coupling reaction. Under moderate conditions, directed self-assembly polymerizations by the transition metal ions Zn2+ and Cd2+, respectively, were carried out. The metallo-supramolecular polymers P1Zn, P1Cd, P2Zn and P2Cd were obtained and fully characterized. The supramolecular polymers P2Zn and P2Cd, containing DPP modified by a phenyl unit, showed absorption maxima at about 504 and 506 nm in films. In contrast, the polymers P1Zn and P1Cd, in which the thiophene moiety-modified DPP was introduced, exhibited strong and broad visible absorption over 300-800 nm with maxima at about 601 and 598 nm and shoulder peaks at about 665 and 671 nm, respectively. The low band gaps estimated from CV of 1.52, 1.51, 1.58 and 1.58 eV for P1Zn, P1Cd, P2Zn and P2Cd, respectively, are also reported.

Narrow band-gap donor-acceptor copolymers based on diketopyrrolopyrrole and diphenylethene: Synthesis, characterization and application in field effect transistor

Zhu, Haoyun,Huang, Wei,Huang, Yuli,Yang, Junwei,Wang, Weizhi

, p. 37 - 44 (2016)

Three low band-gap diketopyrrolopyrrole based polymers with varying donor groups of furan, thiophene and phenyl were synthesized and then copolymerized with diphenylethene. We investigate the influence of different donor groups and comonomers on the band-gap and field effect transistors. The efficient synthesis of the diketopyrrolopyrrole based copolymers was clearly characterized by a variety of measurements. Two dimensional Grazing Incident X-ray Diffraction was measured to prove that furan and thiophene based copolymers have ordered edge-on structure. These copolymers exhibited strong π-π stacking and excellent hole mobilities when applied in the electric double layer field effect transistors. The high mobility of 2.36 cm2 V-1 s-1 with an on/off ratio of 103 was achieved.

1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions

Punzi, Angela,Maiorano, Eliana,Nicoletta, Francesca,Blasi, Davide,Ardizzone, Antonio,Ventosa, Nora,Ratera, Imma,Veciana, Jaume,Farinola, Gianluca Maria

, p. 2617 - 2627 (2016)

1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.

Charge separation and singlet fission in covalently linked diketopyrrolopyrrole derivatives and triphenylamine triad in solution

Bangal, Prakriti Ranjan,Chakali, Madhu,Dyaga, Bharath,Mandal, Haraprasad,Rao, V. Jayathirtha,Venkatesan, Munisamy

, (2021)

A covalently linked push-pull type triad containing two unsymmetrical electron donors, triphenylamine (TPA) and benzothiophene (BT), and diketopyrrolopyrrole (DPP), an electron acceptor, through thiophene spacer has been synthesized (BT-DPP-TPA(7)) and ultrafast relaxation dynamics of the triad has been explored in solution phase by various spectroscopic methods. Steady-state and time-resolved emission studies show the efficient fluorescence quenching of the DPP entity of as prepared BT-DPP-TPA(7) triad. The negative free energy values comprising the redox potentials and singlet state energy of BT-DPP-TPA(7) revealed the probability of electron transfer from the singlet ground state of TPA to the excited singlet state of DPP. Femtosecond transient absorption (fsTA) spectroscopic studies confirmed the formation of charge separation state by detecting triphenylamine radical cation as electron-transfer transients. The rate of charge separation, kCS, is (109?108 s?1) observed to be increasing from nonpolar to polar solvents and the rate of charge recombination, kCR, was found to be slower (μs time scale) in polar solvents like DMF and chloroform, than that in hexane, non-polar solvent (ns time scale). This novel aspect could be due to asymmetrically designed push-pull type triad, a feature that was not evident in push-pull triad constructed using symmetric TPA as electron donors. Furthermore, fsTA studies also demonstrate, for the first time, that the DPP derivatives, TDPP(4) and BT-DPP-TPA(7), both undergo singlet fission (SF) event (S→TT) in 100?200 ps time scale in solution phase for the solution of concentration above ~100 μM. These results may pave the new avenue for device design comprising DPP derivatives.

Incorporation of furan into low band-gap polymers for efficient solar cells

Woo, Claire H.,Beaujuge, Pierre M.,Holcombe, Thomas W.,Lee, Olivia P.,Frechet, Jean M. J.

, p. 15547 - 15549 (2010)

The design, synthesis, and characterization of the first examples of furan-containing low band-gap polymers, PDPP2FT and PDPP3F, with substantial power conversion efficiencies in organic solar cells are reported. Inserting furan moieties in the backbone of the conjugated polymers enables the use of relatively small solubilizing side chains because of the significant contribution of the furan rings to overall polymer solubility in common organic solvents. Bulk heterojunction solar cells fabricated from furan-containing polymers and PC71BM as the acceptor showed power conversion efficiencies reaching 5.0%.

Hetero aromatic donors as effective terminal groups for DPP based organic solar cells

Reddy, Marri Anil,Kumar, Ch. Pavan,Ashok, Akudari,Sharma, Abhishek,Sharma,Chandrasekharam, Malapaka

, p. 9023 - 9036 (2016)

Four new solution-processable donor-acceptor-donor (D-A-D) structured low bandgap small molecules (CSDPP5, CSDPP6, CSDPP7 and CSDPP8) with diketopyrrolopyrrole as central acceptor unit and phenoxazine (POZ) or carbazole (CBZ) as terminal units were designed, synthesized and characterized. The new small molecules have been employed as donors along with the PC71BM as electron acceptor in solution processed BHJ organic solar cells, showed broad absorption bands with suitable electrochemical energy levels. When the BHJ active layer was cast from THF solvent, the optimal power conversion efficiencies obtained with CSDPP5, CSDPP6, CSDPP7 and CSDPP8 are 2.97% 3.06%, 2.42% and 2.43% respectively. The PCE of the devices when processed with DIO/THF solvent, have been further enhanced to 4.69%, 4.14% for CSDPP6:PC71BM and CSDPP8:PC71BM active layers respectively. The enhancement in PCE has been attributed to change in nanoscale morphology and more balanced charge transport resulting from increased hole mobility.

Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: What did we find out?

Kanimozhi, Catherine,Yaacobi-Gross, Nir,Burnett, Edmund K.,Briseno, Alejandro L.,Anthopoulos, Thomas D.,Salzner, Ulrike,Patil, Satish

, p. 17253 - 17265 (2014)

The primary role of substituted side chains in organic semiconductors is to increase their solubility in common organic solvents. In the recent past, many literature reports have suggested that the side chains play a critical role in molecular packing and strongly impact the charge transport properties of conjugated polymers. In this work, we have investigated the influence of side-chains on the charge transport behavior of a novel class of diketopyrrolopyrrole (DPP) based alternating copolymers. To investigate the role of side-chains, we prepared four diketopyrrolopyrrole-diketopyrrolopyrrole (DPP-DPP) conjugated polymers with varied side-chains and carried out a systematic study of thin film microstructure and charge transport properties in polymer thin-film transistors (PTFTs). Combining results obtained from grazing incidence X-ray diffraction (GIXD) and charge transport properties in PTFTs, we conclude side-chains have a strong influence on molecular packing, thin film microstructure, and the charge carrier mobility of DPP-DPP copolymers. However, the influence of side-chains on optical properties was moderate. The preferential "edge-on" packing and dominant n-channel behavior with exceptionally high field-effect electron mobility values of >1 cm2 V-1 s-1 were observed by incorporating hydrophilic (triethylene glycol) and hydrophobic side-chains of alternate DPP units. In contrast, moderate electron and hole mobilities were observed by incorporation of branched hydrophobic side-chains. This work clearly demonstrates that the subtle balance between hydrophobicity and hydrophilicity induced by side-chains is a powerful strategy to alter the molecular packing and improve the ambipolar charge transport properties in DPP-DPP based conjugated polymers. Theoretical analysis supports the conclusion that the side-chains influence polymer properties through morphology changes, as there is no effect on the electronic properties in the gas phase. The exceptional electron mobility is at least partially a result of the strong intramolecular conjugation of the donor and acceptor as evidenced by the unusually wide conduction band of the polymer. the Partner Organisations 2014.

Diketopyrrolopyrrole derivative and application thereof

-

, (2018/12/05)

The invention provides a diketopyrrolopyrrole derivative and application thereof as well as relates to a diketopyrrolopyrrole derivative. The structural formula of the diketopyrrolopyrrole derivativeis as shown in a formula (I): the formula (I) is as shown in the description; in the formula (I), R1 is selected from a group as shown in a formula (I-a), a formula (I-b), a formula (I-c), a formula (I-d) or a formula (I-e) (the formulas are as shown in the description); and in the formula (I-a), the formula (I-b), the formula (I-c), the formula (I-d) and the formula (I-e), * shows connection position. The diketopyrrolopyrrole derivative has excellent photoelectric property and can be applied in the field of organic photoelectric functional devices.

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