Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Aysha, Tarek; Luňák, Stanislav; Lyčka, Antonı́n; Vyňuchal, Jan; Eliáš, Zdeněk; Růžička, Aleš; Padělková, Zdeňka; Hrdina, Radim

doi:10.1016/j.dyepig.2013.04.010

Cited by 21 publications

(21 citation statements)

References 31 publications

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“…The synthesis of all prepared compounds was based on acid-catalysed Aldol condensation and dehydration of commercially avalible isatin with different derivatives of pyrrolinone esters, listed in Scheme 2. The PES esters were synthesised by the procedures described elsewhere [11,17]. The synthesis of 4-bromophenyl PES, shown in Scheme 1, was done differently to Xu et al [20] by a multistep reaction, firstly by the reaction of 4 0 -bromoacetophenone with dimethylcarbonate in a strong basic medium using sodium hydride to obtain the corresponding b-ketoester, and then by the reaction of this b-ketoester with ethyl bromoacetate; the resulting intermediate was cyclised in acetic acid and ammonium acetate to obtain 4-bromophenyl PES [methyl 2-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate] in a good yield of >50%.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

Aysha

El‐Sedik

Mashaly

et al. 2015

Coloration Technology

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A series of new dyes based on the N-analogue of Pechmann hybrid dyes were prepared by the condensation of different 5-aryl derivatives of pyrrolinone ester (phenyl, 4-bromophenyl, thienyl, and biphenyl) with isatin. N-Alkylated derivatives were also prepared using bromoethyl acetate. Full 1 H and 13 C NMR assignment was performed. All prepared dyes were soluble in most organic solvents: N-alkylated derivatives had better solubility than non-alkylated derivatives. The UV-vis absorption spectra of the derivatives under study are quite similar and exhibit maxima in the 509-526 nm range. No E/Z photoisomerisation is observed. The dyeing process, dye exhaustion on polyester, and the fastness properties of the dyes were examined.

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Section: Resultsmentioning

confidence: 99%

“…Ethyl 4,5-dihydro-5-oxo-2-(thiophen-2-yl)-1H-pyrrole-3-carboxylate (thienyl PES in Scheme 2) was prepared using the procedure described elsewhere [11,19]. The synthesis of methyl 2-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate (bromophenyl PES in Scheme 2) was carried out as shown in Scheme 1 [20].…”

Section: Synthesis and Analyticsmentioning

confidence: 99%

Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

Aysha

El‐Sedik

Mashaly

et al. 2015

Coloration Technology

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“…In particular, the LUMO offset between APD and BDT is too large to form a common LUMO (Δ E LUMO = 1.61 eV). More detail is apparent when the benzene rings in APD are replaced by thiophenes giving the unit TAPD (Figure ), as in polymers reported by Cai et al The FMO's of TAPD copolymers with bithiophene ( T2 ) are less localized, as seen in a bathochromic shift of ≈0.4 eV of polymer A 1 against TAPD itself . However, the more extensive calculated FMO delocalization suggested by Cai et al is somewhat exaggerated, as a computational artifact of the very low isosurface values used by the authors to depict the FMO topologies (see the Supporting Information for calculations with parameters similar to those employed here).…”

Section: Resultsmentioning

confidence: 99%

“…The "acceptor" unit under study here is the amidated Pechmann dye ( APD , Figure 2 ). [ 18,19 ] A related system, with terminal thiophene rings ( TAPD ), has met interest in optoelectronics recently, vide infra. [ 20,21 ] The APD core can be considered as a polyene homolog to organic semiconductor building blocks such as diphenyl-diketopyrrolopyrrole ( DPP ) [ 22 ] and isoindigo ( iI ).…”

Section: Resultsmentioning

confidence: 99%

¿Conjugated? Copolymers from a Pechmann Dye Derivative

Liyanage

Milián‐Medina

Zhang

et al. 2016

Macro Chemistry & Physics

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Empirical observation and quantum chemical explanation of a likely common but “overlooked” outcome of the donor–acceptor (D–A) approach to organic electronic materials are reported. The frontier molecular orbitals (FMOs) of D–A copolymers prepared from the amidated Pechmann dye unit (APD) are dictated primarily by this “acceptor,” largely because its HOMO–LUMO gap falls within the gaps of common “donor” units. D–A copolymers with common benzodithiophene and cyclopentadithiophene units as “donors” are presented, giving examples having similar optical properties regardless of backbone planarity and solid‐state packing motif, along with calculations extending to several other common donor monomers to indicate generality. According to quantum‐chemical studies, APD‐localized FMOs form the transition to the lowest excited state, and higher lying charge‐transfer (CT) states. Other existing examples of this FMO situation are likely, but with (opto)electronic properties attributed to lack of conjugation due to, e.g., polymer backbone twisting.

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“…7-10 Such conjugated DA copolymers offer the opportunity for tuning the band-gaps and HOMO/ LUMO energy levels, through varying the donor and acceptor strengths and p-electron topology. [17][18][19][20][21][22] Also indigo as a "natural" dye unit has been incorporated into the backbone of such DA copolymers. [12][13][14][15][16] Despite the great potential of organic solar cells, their limited PCE and environmental stability have to date been the major obstacles to the large-scale commercialization of organic photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

Unusual photophysical properties of conjugated, alternating indigo–fluorene copolymers

et al. 2015

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Alternating indigo-fluorene copolymers have been synthesized by the coupling of didromoindigo and fluorendiboronic ester monomers. The low solubility of the copolymers only allowed for the synthesis of moderate molecular weight copolymers, with a degree of polymerization (DP) up to 11. The syntheses were accomplished through a 10% excess of the fluorene-based monomer component in an AA/BBtype polycondensation mixture. Next, a comprehensive spectroscopic (singlet-singlet and transientfrom fs to msabsorption, fluorescence and phosphorescence spectra) and photophysical investigation (fluorescence, phosphorescence and triplet lifetimes together with fluorescence and triplet occupation and singlet oxygen sensitization quantum yields) of the copolymers was carried out. The experiments were complemented with the spectroscopic results from a fluorene-indigo-fluorene model compound, as well as by TDDFT calculations. Based on our kinetics analysis, singlet energy transfer from the fluorene to indigo moieties is found to be inefficient. Besides the low energy indigo-related absorption band, an additional intermediate energy absorption band is also observed between 400 nm and 500 nm, both for the copolymer and for the model compound. Excitation into this band causes an emission of the indigo moiety. The triplet state is found to be mainly localized at the fluorene moiety; however, the decrease of the phosphorescence quantum yield (f Ph ) when going from the monomeric 9,9bis(dodecyl)fluorene (0.075) to the model trimer (0.003) and copolymer (f Ph ¼ 0.008) suggests that excitation energy transfer occurs in the triplet state. This is further confirmed by the higher level of delocalization of the transient triplet-triplet absorption spectra of the copolymer relative to the monomeric 9,9-bis(dodecyl)fluorene.

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Synthesis, structure, absorption and fluorescence of Pechmann dye heteroanalogues

Cited by 21 publications

References 31 publications

Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

Synthesis, characterisation, and applications of isoindigo/Pechmann dye heteroanalogue hybrid dyes on polyester fabric

¿Conjugated? Copolymers from a Pechmann Dye Derivative

Unusual photophysical properties of conjugated, alternating indigo–fluorene copolymers

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