Color and Chromism of Polydiacetylene Vesicles

Okada, Sheldon Yoshio; Peng, Shuyang; Spevak, and Wayne; Charych, Deborah H.

doi:10.1021/ar970063v

Cited by 564 publications

(569 citation statements)

References 60 publications

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“…The coupling of a recognition event to photoinduced electron transfer or a change in the electronic structure of the conjugated polymer produces changes in the luminescence, UV-visible absorption, or redox potential of the polymer (4, 5). Extensive research has been carried out by using conjugated polymers (derivatives of polydiacetylene, electrochemically polymerized polypyrrole, or polythiophene) as chromic (16)(17)(18)(19) or electrochemical (20)(21)(22)(23)(24)(25)(28)(29)(30)(31) biosensors. However, the relatively low sensitivity of UV-visible absorption measurements, the complex electrochemical instrumentation required, and the nonspecific interactions between biomolecules and conjugated polymers have prevented practical and general use.…”

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confidence: 99%

“…As a result of this sensitivity, conjugated polymers are promising as sensory materials (4,5); sensing may be accomplished by transducing and͞or amplifying physical or chemical changes into electrical, optical, or electrochemical signals. Conjugated polymers have been used to detect chemical species (chemosensors) (6), such as ions (7)(8)(9)(10)(11), gases (for example, trinitrotoluene) (6,(12)(13)(14), and other chemicals (15), or biomolecules such as proteins, antibodies (16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27), and DNA (28-31), using electrical (13,15), chromic (7,8,(16)(17)(18)(19), electrochemical (7-9, 20-25, 28-31), photoluminescent (11,26), chemoluminescent (27), or gravimetric (14) responses.…”

mentioning

confidence: 99%

“…Biosensors based on conjugated polymers as sensory materials exhibit real-time response [electrochemical (20)(21)(22)(23)(24)(25) or optical (16)(17)(18)(19)26)] to the ligand-receptor recognition event. The coupling of a recognition event to photoinduced electron transfer or a change in the electronic structure of the conjugated polymer produces changes in the luminescence, UV-visible absorption, or redox potential of the polymer (4,5).…”

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confidence: 99%

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Biosensors from conjugated polyelectrolyte complexes

Wang

Gong

Heeger

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

284

192

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A charge neutral complex (CNC) was formed in aqueous solution by combining an orange light emitting anionic conjugated polyelectrolyte and a saturated cationic polyelectrolyte at a 1:1 ratio (per repeat unit). Photoluminescence (PL) from the CNC can be quenched by both the negatively charged dinitrophenol (DNP) derivative, (DNP-BS ؊ ), and positively charged methyl viologen (MV 2؉ ). Use of the CNC minimizes nonspecific interactions (which modify the PL) between conjugated polyelectrolytes and biopolymers. Quenching of the PL from the CNC by the DNP derivative and specific unquenching on addition of anti-DNP antibody (anti-DNP IgG) were observed. Thus, biosensing of the anti-DNP IgG was demonstrated.C onjugated polymers are a versatile class of organic materials that promise utility in a variety of applications ranging from antistatic coatings, electrodes, and transistors, to light-emitting diodes, large area displays, photodetectors, photovoltaic cells, and lasers (1-3). The electrical, optical, and electrochemical properties of conjugated polymers can be modified by chemical synthesis and are strongly affected by relatively small perturbations, including changes in temperature, solvent, or chemical environment. As a result of this sensitivity, conjugated polymers are promising as sensory materials (4, 5); sensing may be accomplished by transducing and͞or amplifying physical or chemical changes into electrical, optical, or electrochemical signals. Conjugated polymers have been used to detect chemical species (chemosensors) (6), such as ions (7-11), gases (for example, trinitrotoluene) (6,(12)(13)(14), and other chemicals (15), or biomolecules such as proteins, antibodies (16-27), and DNA (28-31), using electrical (13, 15), chromic (7, 8, 16-19), electrochemical (7-9, 20-25, 28-31), photoluminescent (11, 26), chemoluminescent (27), or gravimetric (14) responses.Contemporary biosensor and bioassay developments have focused on mimicking natural host-receptor (''lock-and-key'') interactions. ''Lock-and-key'' molecular recognition can be between enzyme and substrate, ligand and receptor, antibody and antigen, or between two strands of nucleic acids with complementary sequences. Although antibody-based ELISAs are widely used for detection of biological species with high sensitivity, these assays are relatively labor-intensive and timeconsuming (hours to days) and require two different antibodies of defined specificities to adequately detect the target molecule (potentially making them cumbersome to perform) (32). Additionally, the detection of small molecules using ELISA can seldom be accomplished because of the recognition of one epitope by both capture and detection antibodies. Therefore, competition assays have to be performed that are both less accurate and more time consuming.Biosensors based on conjugated polymers as sensory materials exhibit real-time response [electrochemical (20-25) or optical (16-19, 26)] to the ligand-receptor recognition event. The coupling of a recognition event to photoinduced electron...

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confidence: 99%

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confidence: 99%

See 1 more Smart Citation

Biosensors from conjugated polyelectrolyte complexes

Wang

Gong

Heeger

et al. 2001

Proc. Natl. Acad. Sci. U.S.A.

284

192

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“…In particular, vesicular and tubular assemblies are of much interest because of their unique characteristics as a biomimetic system, carrier for drug or gene, biochemical sensor, electronic or photonic material, nanoreactor, and template for hybrid structure (9-18). Therefore, in these viewpoints, self-assembly of synthetic building blocks by noncovalent interactions is expected to provide a unique methodology for creating supramolecular functional materials (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27).Self-organization of dendrons (6) into supramolecular assemblies has been demonstrated in a thermotropic fashion (19,27), in aqueous phase (21-25), in organic media (20,22,23,26), and at solid-liquid interface (26). Recently, we reported that the amide dendrons can self-organize in various conditions to exhibit a multiplicity of architectures and functions (22-26).…”

mentioning

confidence: 99%

“…vesicle ͉ amphiphile S elf-assembly and transformation of biological or synthetic macromolecules in a wide range of scientific fields are crucial subjects for the achievement of well defined nanostructures and the precise control of the function of supramolecules at the molecular level (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). A multitude of biological or chemical assemblies including vesicle, tubule, fibril, and viral helical coats perform numerous biochemical operations in nature.…”

mentioning

confidence: 99%

Cyclodextrin-covered organic nanotubes derived from self-assembly of dendrons and their supramolecular transformation

Park

Lee

et al. 2006

Proc. Natl. Acad. Sci. U.S.A.

132

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The dendritic building blocks with a focal pyrene unit self-organize into vesicles in aqueous phase. The in situ inclusion of the focal pyrene units into the cavity of ␤-or ␥-cyclodextrin (CD) induces self-assembled organic nanotubes with an average outer diameter of Ϸ45 nm and inner diameter of 22 nm. The surface of the nanotube is covered with CD. Therefore, the functional group on the surface of the nanotube is controlled simply by modifying the functionality of CD. The removal of CD from the nanotube with poly(propylene glycol) reversibly generates vesicles. This work provides an efficient methodology not only to create an additional class of CD-covered organic nanotubes but also to exhibit reversible transformation of nanotubes and vesicles triggered by the motifs of dendron self-assembly, CD inclusion, and pseudorotaxane formation.vesicle ͉ amphiphile S elf-assembly and transformation of biological or synthetic macromolecules in a wide range of scientific fields are crucial subjects for the achievement of well defined nanostructures and the precise control of the function of supramolecules at the molecular level (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). A multitude of biological or chemical assemblies including vesicle, tubule, fibril, and viral helical coats perform numerous biochemical operations in nature. In particular, vesicular and tubular assemblies are of much interest because of their unique characteristics as a biomimetic system, carrier for drug or gene, biochemical sensor, electronic or photonic material, nanoreactor, and template for hybrid structure (9-18). Therefore, in these viewpoints, self-assembly of synthetic building blocks by noncovalent interactions is expected to provide a unique methodology for creating supramolecular functional materials (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27).Self-organization of dendrons (6) into supramolecular assemblies has been demonstrated in a thermotropic fashion (19,27), in aqueous phase (21-25), in organic media (20,22,23,26), and at solid-liquid interface (26). Recently, we reported that the amide dendrons can self-organize in various conditions to exhibit a multiplicity of architectures and functions (22-26). For the preparation of self-assembling nanomaterials, we designed the amide dendritic building blocks consisting of amide branches for hydrogen bonding, carboxyl functionality at the focal point, and alkyl tails for the stabilization of assembled structures by van der Waals interaction (22). Particularly, it was suggested that the dimeric form of the amide dendron, induced by secondary interactions such as hydrogen bonding and -interaction at the focal functional units, is the primary building block in the self-aggregation process in organic media (22,23,26). In addition, the amphiphilic nature of these amide dendritic building blocks provides an opportunity for the formation of various self-assembled nanostructures in aqueous phase. For example, we reported that the transition of the self-organiz...

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Acetylenic Polymers

Liu¹,

Lam²,

Tang³

2011

Encyclopedia of Polymer Science and Technology

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The development of fundamental synthetic chemistry of acetylenic polymers, which not only refers to polyacetylenes but also to all the polymers synthesized from acetylenic monomers containing single or multiple carbon–carbon triple bonds, is summarized in this review. The design of new monomers with one, two, and three triple bonds, explorations of functional tolerant organic and organometallic catalysts, and development of effective linear and nonlinear triple bond‐based polymerization processes have led to successful syntheses of a large variety of acetylenic polymers with miscellaneous structures and advanced specialty properties.

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Color and Chromism of Polydiacetylene Vesicles

Cited by 564 publications

References 60 publications

Biosensors from conjugated polyelectrolyte complexes

Biosensors from conjugated polyelectrolyte complexes

Cyclodextrin-covered organic nanotubes derived from self-assembly of dendrons and their supramolecular transformation

Acetylenic Polymers

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