An internal charge transfer-dependent solvent effect in V-shaped azacyanines

Tasior, Mariusz; Bald, Ilko; Deperasińska, Irena; Cywiński, Piotr; Gryko, Daniel T.

doi:10.1039/c5ob01633a

Cited by 12 publications

(8 citation statements)

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“…The same group also reported the synthesis and study of the optical properties of two bis(styryl)-azacyanines. 21 In this case, the combination of high two-photon absorption cross sections and strong fluorescence QY resulted in good two-photon brightness which opened up the possibility of the use of these dyes as bioimaging agents.…”

Section: Introductionmentioning

confidence: 98%

“…All these findings revealed that the photophysical properties of azacyanines can explicitly be controlled via the substitution of electron-donating/withdrawing groups. The same group also reported the synthesis and study of the optical properties of two bis(styryl)-azacyanines . In this case, the combination of high two-photon absorption cross sections and strong fluorescence QY resulted in good two-photon brightness which opened up the possibility of the use of these dyes as bioimaging agents.…”

Section: Introductionmentioning

confidence: 99%

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Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties

et al. 2020

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Benzothiazoles are known to possess a number of biological activities and therefore are considered to be an important scaffold in the design and synthesis of pharmacophores. In this study, an improved synthesis method for novel fluorescent benzothiazole-based cyclic azacyanine (CAC) dyes bearing different electron-donating/withdrawing groups on their scaffold is presented. The improved method enabled us to increase the synthesis yield for the previously reported CACs. More importantly, it allowed us to synthesize new CAC dyes that were not synthesizable with the previously reported method. The synthesized dyes were characterized by 1 H and 13 C NMR spectroscopy, elemental analysis, and mass spectrometry and their optical (absorption and fluorescence) properties were investigated. All of the synthesized CACs were found to be displaying strong absorption within the range of 387–407 nm. The spectral shifts observed in the absorption and fluorescence measurements suggested that the spectroscopic and optical properties of CACs can be directly modulated by the nature of the electron-donating/withdrawing substituents. The fluorescence quantum yields (QYs) of the unsubstituted (parent CAC) and substituted CACs were also measured and compared. The fluorescence QY of CACs with electron-donating substituents (methoxy or ethoxy) was found to be at least four times higher than that of the parent CAC with no substitutions.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties

et al. 2020

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“…Organic ICT compounds are ideal candidates as third-order nonlinear optical materials because of their inherent high hyperpolarizabilities [35][36][37]. Among these molecules, the quadrupolar D-π-A-π-D structure is highlighted for its excellent nonlinear optical properties [38][39][40][41], with large twophoton absorption (TPA) cross-sections [42,43]. The intramolecular charge transfer, which occurs in systems containing both donor and acceptor parts, will influence the TPA properties strongly [44,45].…”

Section: Introductionmentioning

confidence: 99%

Solvent dependent linear and nonlinear optical properties of triphenylamine unit incorporated difluoroboron β-diketonate complexes

Zhou

Semin³

et al. 2019

Dyes and Pigments

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Article 25fa pilot End User Agreement This publication is distributed under the terms of Article 25fa of the Dutch Copyright Act (Auteurswet) with explicit consent by the author. Dutch law entitles the maker of a short scientific work funded either wholly or partially by Dutch public funds to make that work publicly available for no consideration following a reasonable period of time after the work was first published, provided that clear reference is made to the source of the first publication of the work. This publication is distributed under The Association of Universities in the Netherlands (VSNU) 'Article 25fa implementation' pilot project. In this pilot research outputs of researchers employed by Dutch Universities that comply with the legal requirements of Article 25fa of the Dutch Copyright Act are distributed online and free of cost or other barriers in institutional repositories. Research outputs are distributed six months after their first online publication in the original published version and with proper attribution to the source of the original publication. You are permitted to download and use the publication for personal purposes. All rights remain with the author(s) and/or copyrights owner(s) of this work. Any use of the publication other than authorised under this licence or copyright law is prohibited. If you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons.

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“…In the chemistry of dyes and pigments, systems with extended π-conjugation have prevailed in the literature for years [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. There is, however, an increased interest in weakly coupled systems containing multiple biaryl linkages [ 9 , 10 , 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Photophysical Properties of Weakly Coupled Diketopyrrolopyrroles

et al. 2021

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Three centrosymmetric diketopyrrolopyrroles possessing either two 2-(2′-methoxyphenyl)benzothiazole or two 2-(2′-methoxyphenyl)benzoxazolo-thiophene scaffolds were synthesized in a straightforward manner, and their photophysical properties were investigated. Their emission was significantly bathochromically shifted as compared with that of simple DPPs reaching 650 nm. Judging from theoretical calculations performed with time-dependent density functional theory, in all three cases the excited state was localized on the DPP core and there was no significant CT character. Consequently, emission was almost independent of solvents’ polarity. DPPs possessing 2,5-thiophene units vicinal to DPP core play a role in electronic transitions, resulting in bathochromically shifted absorption and emission. Interestingly, as judged from transient absorption dynamics, intersystem crossing was responsible for the deactivation of the excited states of DPPs possessing para linkers but not in the case of dye bearing meta linker.

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An internal charge transfer-dependent solvent effect in V-shaped azacyanines

Cited by 12 publications

References 50 publications

Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties

Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties

Solvent dependent linear and nonlinear optical properties of triphenylamine unit incorporated difluoroboron β-diketonate complexes

The Synthesis and Photophysical Properties of Weakly Coupled Diketopyrrolopyrroles

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