Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 3: Syntheses of tri- and tetra-aryl DPPs

Riggs, R.L.; Morton, Colin; Slawin, Alexandra M. Z.; Smith, David M.; Westwood, Nicholas J.; Austen, William S.D.; Stuart, Katie E.

doi:10.1016/j.tet.2005.09.005

Cited by 36 publications

(16 citation statements)

References 22 publications

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“…19,23,24 The observed Stokes shifts for dyes 1-8, as shown in Table 2, were in the range of 13 ~ 30 nm which seemed to be larger than similar DPP derivatives containing unsubstituted -NH groups, but to be much smaller values than N,N'-disubstituted derivatives, for example, Stokes shift of 11 nm was reported for unsubstituted DPP, whereas N,N-dimethylated analogue exhibited a greater shift of 43 nm. [24][25][26] In this series, the most shifts were found in dyes 2b, 3a, 3b, 5 which indicated their smaller difference of energy between the lowest vibrational level of the excited state S1 and vibrational levels of the ground state comparing to other dyes.…”

Section: Notesmentioning

confidence: 85%

“…[12][13][14] Single crystal X-ray structural studies [14][15][16] on DPP clearly reveal the existence of chains of hydrogen bonds between the N-H of one molecule and the oxygen of another molecule which mainly contributes to excellent thermal stability and lack of solubility in most solvents. Therefore, the cancellation of the intermolecular hydrogen bonding via N-methylation [16][17][18] or N-arylation 19,20 of DPP yields not only more soluble derivatives, in the order DPP ≪ N-monomethyl-DPP ≪ N,N'-dimethyl-DPP, but also less thermal stable analogues.…”

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confidence: 99%

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Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group

Choi¹,

Kwon²,

Kim³

et al. 2010

Bulletin of the Korean Chemical Society

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Section: Notesmentioning

confidence: 85%

mentioning

confidence: 99%

Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group

Choi¹,

Kwon²,

Kim³

et al. 2010

Bulletin of the Korean Chemical Society

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“…Analogous to this tautomeric equili-brium have been observed. 11 ' 12 The reverse enamineimine tautomerism has also been reported 13 .These dicyanoethylenes 4 upon treating with triethylamine were converted, through a Thorpe-Ziegler cyclization to the corresponding 3-aminopyrroles 5, which were also prepared directly from the preparation reaction of dicyanoethylenes 4 by treating the reaction mixture with an additional amount of triethylamine (see experimental).…”

mentioning

confidence: 75%

A New Route to the Synthesis of 3-Aminomethylene Derivatives of 2-Cyano-3-Phenylacrylonitriles and the Polyfunctionalized Pyrroles Synthesis Thereof

Tsolomiti¹,

Tsolomiti²,

Tsolomitis³

2007

Heterocyclic Communications

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“…Among the different synthetic routes to the DPP moiety [104][105][106][107][108] , the most commonly employed method uses aromatic nitriles with a succinic ester in the presence of a strong base 104,109 and this was selected for the synthesis of the series, of the compounds described in this thesis. The first step in the synthesis of DPP core with two thiophenes attached was therefore the formation of the 2-cyanothiophene 2.6, and two routes were investigated (Scheme 2.1).…”

Section: Synthesis Of Dpp(th) 2 With 2-ethylhexyl Solubilising Groupsmentioning

confidence: 99%

Low optical gap materials for organic solar cells - research and application

Chandrasekharan¹

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In spite of the cost of silicon solar cells decreasing in recent years, there is considerable interest in solar cells with lightweight and flexible forms. Organic semiconductor-based photovoltaic cells (OPVs) have the potential to offer low cost, lightweight and flexible devices. At this stage there is still much to be improved for OPVs as the efficiencies are still lower than their inorganic counterparts. Polymeric materials have been more widely studied than their non-polymeric counterparts. In recent years OPVs polymeric donor materials have emerged with efficiencies reaching 10% with quite a range of materials now providing efficiencies of around 7%. However, the problem with semiconducting polymers is that control of the regioregularity, poly(dispersity), and molecular weight from batch-to-batch is not a simple process. Solution-processable nonpolymeric semiconductors are attractive for opto-electronic applications as they are simpler to synthesise, purify, characterise, and the optical properties can be more easily fine-tuned. In this context, diketopyrrolopyrrole (DPP) based small molecules have shown promising results with devices efficiencies reaching around 5-6%. Key properties of the DPP unit are strong π-π interactions, and suitable and tunable energy levels. These properties have been the main drivers in their use in OPVs.This thesis consist of the synthesis, characterisation, and bulk hetrojunction (BHJ) devices properties of novel DPP(ThAr) 2 non-polymeric materials. Accordingly, a first series of compounds was synthesized with different electron affinity groups such as fluorenone (Fl) [EhDPP(ThFl) 2 and OddDPP(ThFl) 2 ] and benzothiadiazole (Bt) [OddDPP(ThBt) 2 ] attached to the distal ends of a bisthienyl-diketopyrrolopyrrole unit DPP(Th) 2 unit. The 'DPP(ThAr) 2 ' derivatives were synthesised under standard Suzuki-Miyaura cross-coupling or by direct arylation reaction conditions and the rate of the direct arylation reaction was found to be faster than for the Suzuki-Miyaura crosscoupling reactions. The solubility of the compounds was poor when the 2-ethylhexyl (Eh) moiety was used as the solubilising group for DPP(ThFl) 2 . 2-Octyldodecyl (Odd) solubilising groups gave better solubility in chlorinated solvents, which are typically used in OPV fabrication. The three nonpolymeric DPP materials exhibited bipolar charge transport in organic field effect transistors (OFETs), with hole and electron mobility in the order of 10 -2 −10 -3 cm 2 V -1 s -1 , and in a diode architecture OddDPP(ThFl) 2 and OddDPP(ThBt) 2 exhibited mobilities of the order of 10 -4 cm 2 V -1 s -1 for pristine films. In BHJ devices using [6,6]-phenyl-C70-butyric acid methyl ester (PC70BM)as the acceptor, different solvent mixtures were used for device fabrication to achieve the maximum efficiency. The EQE spectra of the blend film suggested that charge generation due to absorption at iii wavelengths longer than 750 nm occurred through the Channel I pathway, and at wavelengths shorter than 750 nm, both Channel I and II ...

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Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 3: Syntheses of tri- and tetra-aryl DPPs

Cited by 36 publications

References 22 publications

Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group

Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group

A New Route to the Synthesis of 3-Aminomethylene Derivatives of 2-Cyano-3-Phenylacrylonitriles and the Polyfunctionalized Pyrroles Synthesis Thereof

Low optical gap materials for organic solar cells - research and application

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