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

Choi, Se-Hwa; Kwon, Oh-Tak; Kim, Na-rim; Yoon, C. S.; Kim, Jae-Pil; Choi, Jae‐Hong

doi:10.5012/bkcs.2010.31.04.1073

Cited by 14 publications

(3 citation statements)

References 9 publications

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“…Hence, the observed shi in the absorption bands is attributed to solvatochromism. However, solvatochromism is only signicant in the dipolar dyads 9b and 9c, although it is negative, which suggests existence of a more polar ground state of these compounds compared to the corresponding excited states, [80][81][82] suggesting that the ground state is already a strong charge transfer state represented by the quinoidal forms (Fig. 5 and 6) as has indeed been described for similar dicyanovinyl chromophore.…”

Section: Resultssupporting

confidence: 55%

“…86 Also, polar protic solvents are capable of hydrogen bonding with the available lone pairs, hence stabilizing the ground state more than the excited state. 80 Electrochemistry Electrochemistry was performed in DCM (freshly distilled from CaH 2 ), with 2 Â 10 À2 M tetrabutyl ammonium hexa-uorophosphate (TBAPF 6 ) as a supporting electrolyte (Aldrich, Electrochemical grade). A platinum electrode was used both as working as well as counter electrode and Ag/AgCl as reference electrode (CHI660D Electrochemical Workstation).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, linear and nonlinear optical properties of thermally stable ferrocene-diketopyrrolopyrrole dyads

et al. 2015

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A set of new ferrocene-diketopyrrolopyrrole (Fc-DPP) conjugated dyads was synthesized and their optical, nonlinear optical (NLO) and electrochemical properties were investigated. The second-order nonlinear polarizabilities were determined using Hyper-Rayleigh Scattering with femtosecond pulsed laser light at 840 nm. The dyads depicted structure dependent NLO response, which could be explained by correlating optical as well as electrochemical data. In the latter case, it is shown that the amplitude of the Fc based one-electron redox process of D-π-A type dyads is doubled in the dyads of the type D-π-A-π-D, where the acceptor (DPP) is flanked by two Fc donors. Please do not adjust marginsPlease do not adjust margins diisopropyl succinate (8.10 g, 40 mmol) over a period of 1 h. Reaction mixture was heated at 85 °C for 2 h, after which it was cooled to 50 °C and 50 ml methanol was added. The reaction mixture was neutralized using glacial acetic acid and stirred for 15 min. and then cooled to ambient temperature and the contents were filtered over sintered glass (G4) funnel. Residue was washed twice with hot methanol and de-ionized water to yield analytically pure dark red solid 1 (61%). Mp> 300 o C IR (KBr): ν max 1628, 1648, 3153 and 3417 cm -1 .

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Section: Resultssupporting

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Synthesis, linear and nonlinear optical properties of thermally stable ferrocene-diketopyrrolopyrrole dyads

et al. 2015

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“…[12,13] Thus, the compounds present a multitude of opportunities for structural and electronic modification via synthetic functionalization, such as end capping of the aromatic sections, [14,15] the addition of conjugated flanking units to extend charge delocalization [16,17] and solubilizing chains of varying polarity at the N position to aid processing. [18] This alkylation of DPP derivatives gives rise to solubility in relatively low polarity organic solvents, [19][20][21] as well as solubility in more polar solvents when heteroatom-containing chains are appended. [22,23] Appropriate substitution can modulate both intra-and inter-molecular interactions in the solid state.…”

Section: Introductionmentioning

confidence: 99%

Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies

et al. 2019

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A series of symmetrically bis‐4‐methoxybenzyl (4MB) N‐substituted 1,4‐diketopyrrolo[3,4‐c]pyrrole (DPP) derivatives have been synthesized. The 4MB unit makes the DPP core soluble, and shows subtle modification of up to 0.2 eV in ground and excited states of the core when compared with related alkyl derivatives. Absorption and emission spectroscopy, as well as electrochemical and computational methods have been employed to prove the importance of the peripheral aryl units on the donor/ acceptor properties of the molecules. The 4MB products are highly fluorescent (quantum yields approaching 100 % in solution), with a unique distribution of frontier states shown by spectroelectrochemistry. The solid‐state fluorescence correlates with the X‐ray crystal structures of the compounds, a Stokes shift of approximately 80 nm is seen for two of the compounds. The frontier energy levels show that this subtle substitutional change could be of future use in molecular energy level tailoring in these, and related, materials for organic (opto)electronics.

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Comparative study of the optoelectronic properties of diketopyrrolopyrrole based polymers obtained by direct C-H arylation

Shaker

2021

Polym. Bull.

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

Cited by 14 publications

References 9 publications

Synthesis, linear and nonlinear optical properties of thermally stable ferrocene-diketopyrrolopyrrole dyads

Synthesis, linear and nonlinear optical properties of thermally stable ferrocene-diketopyrrolopyrrole dyads

Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies

Comparative study of the optoelectronic properties of diketopyrrolopyrrole based polymers obtained by direct C-H arylation

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