Self-organizing surface-initiated polymerization of perylenediimides on indium tin oxides

Charbonnaz, Pierre; Sakai, Naomi; Matile, Stefan

doi:10.1039/c2sc01047j

Cited by 23 publications

(18 citation statements)

References 37 publications

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“…In this protocol, UV irradiation of a thin film of monomers comprised of a PDI‐containing two pendent acrylate moieties generates a solvent‐resistant polymer film that can be utilized in fabrication of an efficient solar cell. In another approach, surface‐initiated polymerization involving ring opening of cyclic disulfides was employed to construct a polymer that contains PDI groups . Although the main purpose of this effort was to produce systems containing stacked PDI molecules, the strategy is of potential use for generation of a variety of stabilized PDI constructs.…”

Section: Introductionmentioning

confidence: 99%

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

Seo

Kantha

Joung

et al. 2019

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Because of their unique structural and optical properties, 1D perylene diimide (PDI) derivatives have gained attention for use in optoelectronic devices. However, PDI‐containing self‐assembled supramolecular systems often are of limited use because they have supramolecular architectures that are held together by weak noncovalent π–π stacking, hydrogen bonding, and hydrophobic interactions. As a result, they are intrinsically unstable under solution‐processing conditions. To overcome this limitation, a polydiacetylene (PDA)‐based strategy is developed to construct a solvent‐resistant and stable PDI assembly. For this purpose, first the monomer PDI–BisDA is generated, in which two polymerizable diacetylene (DA) units are covalently linked to a PDI core. Importantly, 254 nm UV irradiation of self‐assembled PDI–BisDA nanofibers forms solvent‐resistant and stable PDI–PDA fibers. Owing to the presence of PDA, the generated polymer fibers display an increased photocurrent. In addition, the existence of PDA and PDI moieties in the fiber leads to the occurrence of switchable on–off fluorescence resonance energy transfer (FRET) between the PDI and reversibly thermochromic PDA chromophores.

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Section: Introductionmentioning

confidence: 99%

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

Seo

Kantha

Joung

et al. 2019

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“…Moreover, the SOSIP methodology used to build the central stack is not limited to NDIs (e.g., PDIs, oligothiophenes), 15,16 all components of the triad can therefore be quite easily varied. Judged from results with simpler systems, 19,20 the installation of oriented, antiparallel redox gradients in the two channels added by TSE should be very straightforward.…”

Section: ■ Conclusionmentioning

confidence: 99%

Toward Oriented Surface Architectures with Three Coaxial Charge-Transporting Pathways

et al. 2013

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We report a synthetic method to build oriented architectures with three coaxial π-stacks directly on solid surfaces. The approach operates with orthogonal dynamic bonds, disulfides and hydrazones, self-organizing surface-initiated polymerization (SOSIP), and templated stack-exchange (TSE). Compatibility with naphthalenediimides, perylenediimides, squaraines, fullerenes, oligothiophenes, and triphenylamine is confirmed. Compared to photosystems composed of two coaxial channels, the installation of a third channel increases photocurrent generation up to 10 times. Limitations concern giant stack exchangers that fail to enter SOSIP architectures (e.g., phthalocyanines surrounded by three fullerenes), and planar triads that can give folded or interdigitated charge-transfer architectures rather than three coaxial channels. The reported triple-channel surface architectures are as sophisticated as it gets today, the directionality of their construction promises general access to multichannel architectures with multicomponent gradients in each individual channel. The reported approach will allow us to systematically unravel the ultrafast photophysics of molecular dyads and triads in surface architectures, and might become useful to develop conceptually innovative optoelectronic devices.

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“…Self‐organizing surface‐initiated polymerization turned out to provide general access to ordered and oriented surface architectures that generate much more photocurrent than their disordered controls. Experimental evidence for compatibility with other stacks (perylenediimides and oligothiophenes), expandable and exchangeable surroundings including additional stacks, oriented multicomponent gradients, antiparallel double‐gradient systems as well as self‐repair and reactivation exists. Self‐sorting on surfaces was explored with SOSIP copolymerization (co‐SOSIP) .…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Self‐Sorting on Surfaces: Transcription of Chiral Information

2012

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Templated self-sorting on surfaces has been introduced recently as a new approach to construct multicomponent architectures directly on solid oxide surfaces. In this process, two-dimensional information placed on the surface is transcribed into three-dimensional architectures with up to 97% intrinsic templation efficiency. Previously, we have shown that isosteric partners of different color do neither self-sort nor respond to templation during self-organizing surface-initiated copolymerization (co-SOSIP). To evaluate the importance of chirality in this process, co-SOSIP with mixtures of pseudo-enantiomers of isosteric partners is explored. The composition of the obtained SOSIP architectures is independent of the composition of the initiator mixtures on the surface. This absence of templation from the surface rules out the occurrence of uniform self-sorting of pseudo-enantiomeric isosters, a process similar to chiral resolution in conglomerates. Alternate self-sorting, the complementary process comparable with racemic crystallization, is indistinguishable from random mixing in structural studies. However, different photocurrent generation by pseudo-racemic compared with pseudo-homochiral photosystems support, on the functional level, that alternate self-sorting occurs with pseudo-enantiomeric partners. These results support that chirality is important for the transcription of two-dimensional information into three-dimensional architectures and suggest that alternate self-sorting dominates over uniform self-sorting as racemic crystallization dominates over chiral resolution.

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Self-organizing surface-initiated polymerization of perylenediimides on indium tin oxides

Cited by 23 publications

References 37 publications

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

Covalently Linked Perylene Diimide–Polydiacetylene Nanofibers Display Enhanced Stability and Photocurrent with Reversible FRET Phenomenon

Toward Oriented Surface Architectures with Three Coaxial Charge-Transporting Pathways

Stereoselective Self‐Sorting on Surfaces: Transcription of Chiral Information

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