Synthetic Routes to TEG‐Substituted Diketopyrrolopyrrole‐Based Low Band‐Gap Polymers

Punzi, Angela; Nicoletta, Francesca; Marzano, Giuseppina; Fortuna, Cosimo G.; Dagar, Janardan; Brown, Thomas M.; Farinola, Gianluca M.

doi:10.1002/ejoc.201600406

Cited by 30 publications

(16 citation statements)

References 75 publications

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“…17,18 Alternatively, in very few reported cases, water-insoluble DPP molecules have been processed as nanoparticles with reduced ACQ effect, for application in in vitro and in vivo bioimaging. 16,19 In this context , and following our previous works on development of organometallic protocols for functionalized conjugated structures, [20][21][22][23][24] we recently published a study on the self-assembly process of several amphiphilic red-emitting DPP derivatives, with the formation of H-and Jaggregates in thin-films and organic nanoparticles (ONPs). 25 Unfortunately, upon dispersion in water, all these molecules show a severe ACQ effect, due to the intense π-π stacking of the rigid conjugated structures.…”

Section: Introductionmentioning

confidence: 99%

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Ardizzone

Blasi

Vona

et al. 2018

Chemistry A European J

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Diketopyrrolopyrroles (DPPs) have recently attracted much interest as very bright and photostable red-emitting molecules. However, their tendency to form nonfluorescent aggregates in water through the aggregation-caused quenching (ACQ) effect is a major issue that limits their application under the microscope. Herein, two DPP molecules have been incorporated into the membrane of highly stable and water-soluble quatsomes (QS; nanovesicles composed of surfactants and sterols), which allow their nanostructuration in water and, at the same time, limits the ACQ effect. The obtained fluorescent organic nanoparticles showed superior structural homogeneity, along with long-term colloidal and optical stability. A thorough one- (1P) and two-photon (2P) fluorescence characterization revealed the promising photophysical features of these fluorescent nanovesicles, which showed a high 1P and 2P brightness. Finally, the fluorescent QSs were used for the in vitro bioimaging of Saos-2 osteosarcoma cell lines; this demonstrates their potential as nanomaterials for bioimaging applications.

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Section: Introductionmentioning

confidence: 99%

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Ardizzone

Blasi

Vona

et al. 2018

Chemistry A European J

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“…A similar DPP‐thiophene polymer was also prepared by the same group in 2017 under robust biphasic conditions as previously discussed [42] . Farinola's group also prepared DPP – thiophene based polymers, with the side chain of triethylene glycol (TEG) instead of alkyl side chains because of TEG's ability to act as stack‐inducing agents, and improve self‐assembling [62] . The resultant polymer exhibited low band gaps with absorption maxima exceeding 700 nm.…”

Section: Direct Arylation Polymerization (Darp)mentioning

confidence: 96%

“…[42] Farinola's group also prepared DPP -thiophene based polymers, with the side chain of triethylene glycol (TEG) instead of alkyl side chains because of TEG's ability to act as stack-inducing agents, and improve self-assembling. [62] The resultant polymer exhibited low band gaps with absorption maxima exceeding 700 nm. Michinobu's group reported DPP -thiophene -fluorene and DPPthiophene -phenylaniline polymers A9d and A9e prepared by microwave assisted DArP with molecular weights of 12.6 kg/mol and 7.9 kg/mol, respectively (Scheme 9b).…”

Section: Polymers Containing the Diketopyrrolopyrrole (Dpp) Moietymentioning

confidence: 99%

Synthesis of Conjugated Polymers via Transition Metal Catalysed C−H Bond Activation

Chua

Png

Zhu

et al. 2021

Chemistry An Asian Journal

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Transition metal catalysed CÀ H bond activation chemistry has emerged as an exciting and promising approach in organic synthesis. This allows us to synthesize a wider range of functional molecules and conjugated polymers in a more convenient and more atom economical way. The formation of CÀ C bonds in the construction of piconjugated systems, particularly for conjugated polymers, has benefited much from the advances in CÀ H bond activation chemistry. Compared to conventional transitionmetal catalysed cross-coupling polymerization such as Suzuki and Stille cross-coupling, pre-functionalization of aromatic monomers, such as halogenation, borylation and stannylation, is no longer required for direct arylation polymerization (DArP), which involve CÀ H/CÀ X cross-coupling, and oxidative direct arylation polymerization (Ox-DArP), which involves CÀ H/CÀ H cross-coupling protocols driven by the activation of monomers' C(sp 2 )À H bonds. Furthermore, poly(annulation) via CÀ H bond activation chemistry leads to the formation of unique pi-conjugated moieties as part of the polymeric backbone. This review thus summarises advances to date in the synthesis of conjugated polymers utilizing transition metal catalysed CÀ H bond activation chemistry. A variety of conjugated polymers via DArP including poly(thiophene), thieno [3,4-c]pyrrole-4,6-dione)-containing, fluorenyl-containing, benzothiadiazole-containing and diketopyrrolopyrrolecontaining copolymers, were summarized. Conjugated polymers obtained through Ox-DArP were outlined and compared. Furthermore, poly(annulation) using transition metal catalysed CÀ H bond activation chemistry was also reviewed. In the last part of this review, difficulties and perspective to make use of transition metal catalysed CÀ H activation polymerization to prepare conjugated polymers were discussed and commented.

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“…Looking for chromophores, which possess the suitable architecture for probing via weakening of their intramolecular electronic coupling, we focused on diketopyrrolopyrrole (DPP) derivatives ( Figure 1 ) [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. These donor–acceptor cross-conjugated dyes with DPP cores are characterized by straightforward synthesis [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ], almost a unity emission quantum yield [ 21 ], large two-photon absorption cross-section [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ], and broad utility in organic optoelectronics [ 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , …”

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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Synthetic Routes to TEG‐Substituted Diketopyrrolopyrrole‐Based Low Band‐Gap Polymers

Cited by 30 publications

References 75 publications

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Highly Stable and Red‐Emitting Nanovesicles Incorporating Lipophilic Diketopyrrolopyrroles for Cell Imaging

Synthesis of Conjugated Polymers via Transition Metal Catalysed C−H Bond Activation

The Synthesis and Photophysical Properties of Weakly Coupled Diketopyrrolopyrroles

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