Advances in polydiacetylene development for the design of side chain groups in smart material applications – a mini review

Deng, Qigen; Fan, Ting; He, Guozhang; Hu, Xiaohong; Hong, Xiaxiao; Chen, Hong; Luo, Shi‐He; Wang, Zhao‐Yang; Huo, Jingpei

doi:10.1039/c7py01396e

Cited by 70 publications

(62 citation statements)

References 70 publications

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“…We recently described a new strategy for fabrication of patterned conducting polymers and magnetic nanoparticles that takes advantage of the photopolymerization property of self‐assembled diacetylenes (DA). It is well known that topochemical polymerization of self‐assembled DAs leads to formation of polydiacetylene (PDA) . Because DAs are typically soluble in most organic solvents and PDAs are not, non‐UV‐irradiated parts of films created in this manner can be removed by utilizing a solvent development protocol.…”

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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“…While some natural furan-based diacetylene (DA) do exist [38][39][40], no attempts to polymerize them have been reported. This seems quite surprising since polydiacetylene (PDA) has attracted tremendous attention for applications in various fields [41,42] due to its unique chromatic [43][44][45][46][47][48][49][50] and semi-conductive properties [51][52][53][54][55][56][57][58][59][60][61].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

et al. 2019

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Crystal structure elucidations of bio-based polymers provide invaluable data regarding structure-property relationships. In this work, we achieved synthesis and Single Crystal X-ray Diffraction (SCXRD) structural determination of a new furan-based polydiacetylene (PDA) derivative with carbamate (urethane) functionality. Firstly, diacetylene (DA) monomers were found to self-assemble in the crystalline state in such a way that the polymerization theoretically occurred in two different directions. Indeed, for both directions, geometrical parameters for the reactive alignment of DA are satisfied and closely related with the optimal geometrical parameters for DA topochemical polymerization (d(1) = 4.7-5.2 Å, d(2) ≤ 3.8 Å, θ ≈ 45 • ). However, within the axis of hydrogen bonds (HB), the self-assembling monomers display distances and angles (d(1) = 4.816 Å, d(2) = 3.822 Å, θ = 51 • ) that deviate more from the ideal values than those in the perpendicular direction (d(1) = 4.915Å, d(2) = 3.499Å, θ ≈ 45 • ). As expected from these observations, the thermal topochemical polymerization occurs in the direction perpendicular to the HB and the resulting PDA was characterized by SCXRD.

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“…Based on these characteristics, Charych et al first applied PDA bilayer assembly on colorimetric detection of a receptor–ligand interaction . Most of the later studies using PDA as sensing materials, the resulting signals were performed as absorption or fluorescence with broad spectra . Hence, an analysis tool with narrow spectra will be a powerful supplement.…”

mentioning

confidence: 99%

“…The fluorescence level which appeared in Raman spectra is calculated (see the Supporting Information). The chromatic property of PDA in response to external stimulus has previously been quantified using colorimetric response (CR) . In addition, the PL can be quantified as its intensity increases upon phase transition.…”

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confidence: 99%

Monitoring Based on Narrow‐Band Resonance Raman for “Phase‐Shifting” π‐Conjugated Polydiacetylene Vesicles upon Host–Guest Interaction and Thermal Stimuli

Cui

Hong

Ahn

2018

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The present study reports a quantified monitoring by means of in situ resonance Raman scattering that analyzes phase-shifting characteristics of π-systems upon interacting with target analytes. A chemo- and thermochromic polydiacetylene vesicular probe is evaluated with multiple-wavelength Raman scattering modes in resonance with its phases, respectively, and thus can trace the phase-shifts. This Raman scattering-based analytical quantification is also successful in monitoring host-guest recognition events by utilizing much narrower bands, compared to those in conventional absorption or photoluminescence (PL) methods. As one of the outcomes, the monitoring analysis overcomes the limitations based on widely used colorimetric response (%CR) or PL that failed in the case of interaction with a surfactant, CTAB.

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Advances in polydiacetylene development for the design of side chain groups in smart material applications – a mini review

Abstract: This review focuses on various side chain groups based on PDAs published over the last 3 years, covering urea, melamine, ferriferous oxide and coumarin. Perspectives on the remaining challenges and future developments are also proposed.

Cited by 70 publications

References 70 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

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

Monitoring Based on Narrow‐Band Resonance Raman for “Phase‐Shifting” π‐Conjugated Polydiacetylene Vesicles upon Host–Guest Interaction and Thermal Stimuli

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