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Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis-Resorcinol Coupler.

ABSTRACT: The reaction-based deposition on various surfaces of an all-organic fluorescent coating is reported here, involving autoxidation of 2 mM dopamine in carbonate buffer at pH 9.0, in the presence of a 1 mM diamine-resorcinol coupler (Bis-Res) prepared from 2,4-dihydroxybenzaldehyde and hexamethylenediamine (HMDA). Spectral analysis of the films coupled with an LC-MS investigation of the yellow fluorescent mixture was compatible with the formation and deposition of HMDA-linked methanobenzofuroazocinone fluorophores. Both the emission properties and hydrophobicity of the film were abated in a reversible manner following exposure to acid vapors. These results provide an entry to efficient and practical fluorescent coating methodologies based on in situ generation and the deposition of wet adhesive, as well as fluorescent materials combining a strongly emitting fluorophore with the film-forming properties of long chain diamines.

SUBMITTER: Alfieri ML

PROVIDER: S-EPMC6769982 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Hexamethylenediamine-Mediated Polydopamine Film Deposition: Inhibition by Resorcinol as a Strategy for Mapping Quinone Targeting Mechanisms.

Project description:Hexamethylenediamine (HMDA) and other long chain aliphatic diamines can induce substrate-independent polymer film deposition from dopamine and several other catechols substrates at relatively low concentrations, however the mechanism of the diamine-promoted effect has remained little understood. Herein, we report data indicating that: (a) film deposition from 1 mM HMDA and dopamine is not affected by chemical oxidation with periodate but is markedly inhibited by resorcinol, which also prevents PDA film formation at 10 mM monomer concentration in the absence of HMDA; (b) N-acetylation of HMDA completely inhibits the effect on PDA film formation; (c) HMDA enables surface functionalization with 1 mM 5,6-dihydroxyindole (DHI) polymerization at pH 9.0 in a resorcinol-inhibitable manner. Structural investigation of the polymers produced from dopamine and DHI in the presence of HMDA using solid state 13C and 15N NMR and MALDI-MS suggested formation of covalent cross linked structures. It is concluded that HMDA enhances polydopamine adhesion by acting both on dopamine quinone and downstream, e.g., via covalent coupling with DHI. These results provide new insights into the mechanisms of PDA adhesion and disclose resorcinol as a new potent tool for targeting/mapping quinone intermediates and for controlling polymer growth.

| S-EPMC6560077 | biostudies-literature

Janus metallic film with gold and silver luster by electroless deposition of silver using poly(dopamine acrylamide) thin film.

Project description:Films that exhibit different metallic luster on the front and back, called Janus metallic films, have broad applications ranging from design materials to optical devices. However, the fabrication of these films is often a complicated process involving multiple metal deposition steps, thermal annealing, and calcination. Herein, we report the simple preparation of a Janus metallic film by electroless deposition of silver on a poly(dopamine acrylamide) (pDOPAm) thin film. pDOPAm was successfully synthesized via the controlled reversible addition-fragmentation chain transfer polymerization of dopamine acrylamide without a protective group using dimethylformamide as the solvent. The synthesized pDOPAm was spin-coated onto a solid substrate, which was then immersed in an aqueous AgNO3 solution to achieve the electroless deposition of silver. Our preparation method will considerably simplify the fabrication of Janus metallic films, enabling their widespread application as decorative or authentication materials.

| S-EPMC10517145 | biostudies-literature

Kinetic Study of the Maillard Reaction in Thin Film Generated by Microdroplets Deposition.

Project description:The Maillard reaction kinetics in the confined volume of the thin film produced by ESI microdroplet deposition was studied by mass spectrometry. The almost exclusive formation of the Amadori product from the reaction of D-xylose and D-glucose toward L-glycine and L-lysine was demonstrated. The thin film Maillard reaction occurred at a mild synthetic condition under which the same process in solution was not observed. The comparison of the thin film kinetics with that of the reaction performed in solution showed strong thin film rate acceleration factors.

| S-EPMC9504576 | biostudies-literature

(μ-Ethane-1,2-diamine-κN:N')bis-[bis-(ethane-1,2-diamine-κN,N')zinc(II)] tetra-kis-(perchlorate).

Project description:In the title salt, [Zn(2)(C(2)H(8)N(2))(5)](ClO(4))(4), an ethyl-enediamine mol-ecule bridges two bis-(ethyl-enediamine)-zinc units; the five-coordinate Zn atoms show a trigonal-bipyramidal coordination geometry that is distorted towards square-pyramidal (that of one Zn atom is distorted by 12% and that of the other by 34%). The perchlorate ions are all disordered over two positions in a 1:1 ratio. The cation inter-acts weakly with the anion by N-H⋯O hydrogen bonds, generating a three-dimensional network.

| S-EPMC3009181 | biostudies-literature

Diazido-bis(propane-1,3-diamine)copper(II).

Project description:In the title complex, [Cu(N(3))(2)(C(3)H(10)N(2))(2)], the Cu(II) ion resides on a centre of symmetry and is in a Jahn-Teller distorted octa-hedral coordination environment comprising two N atoms from azide anions in axial positions and four N atoms from propane-1,3-diamine (tn) ligands in equatorial positions. Inter-molecular N-H?N hydrogen bonds produce R(2) (1)(6), R(2) (2)(8), R(2) (2)(12) and R(4) (2)(8) rings, generating a two-dimensional layer.

| S-EPMC2984027 | biostudies-literature

Bis(acetato-?O)bis-(4,5-dimethyl-benzene-1,2-diamine-?N)zinc.

Project description:The structure of the title compound, [Zn(CH(3)COO)(2)(C(8)H(12)N(2))(2)], has one half molecule in the asymmetric unit. The Zn(II) atom is situated on a twofold rotation axis and is tetrahedrally coordinated by two N and two O atoms. The crystal packing displays inter-molecular N-H?O hydrogen bonds and intra-molecular N-H?O and N-H?N hydrogen bonding.

| S-EPMC3414110 | biostudies-literature

Diaqua-bis-(propane-1,3-diamine)-nickel(II) bis-(propane-1,3-diamine)-disulfato-nickelate(II).

Project description:The ionic Ni(II) title complex, [Ni(C(3)H(10)N(2))(2)(H(2)O)(2)][Ni(SO(4))(2)(C(3)H(10)N(2))(2)], is built up of [Ni(dipr)(2)(H(2)O)(2)](2+) complex cations and [Ni(dipr)(2)(SO(4))(2)](2-) complex anions (dipr is propane-1,3-diamine). Both Ni(II) atoms display a slightly distorted octa-hedral coordination and are located on inversion centers. There are several types of hydrogen-bonding inter-actions, which connect complex cations and anions into a two-dimensional network parallel to (010). Hydrogen bonds formed by the axially coordinated water mol-ecule of the complex cation and one of the O atoms of the sulfate groups of the complex anion (first type) link them into chains along the c axis. These chains are linked to each other through hydrogen bonds formed by an O atom (second type) of the SO(4) groups and NH(2) groups of the ligand of the complex cations from neighboring chains, forming a two-dimensional hydrogen-bonded net perpendicular to the b axis. The third type of O atoms of the sulfate groups of the complex anion are also linked into chains by a combination of both previously described types of H-atom connections.

| S-EPMC3343811 | biostudies-other

[μ-N,N'-Bis(2-pyridylmethyl-ene)ethane-1,2-diamine]bis-{aqua-[N,N'-bis-(2-pyridyl-methyl-ene)ethane-1,2-diamine]manganese(II)} tetra-kis(perchlorate).

Project description:The cation of the salt, [Mn(2)(C(14)H(14)N(4))(3)(H(2)O)(2)](ClO(4))(4), lies on a center of inversion, the center lying midway along the ethyl-ene chain of the bridging N,N'-bis-(2-pyridylmethyl-ene)ethane-1,2-diamine ligand. The Mn atom is chelated by two atoms N atoms of this bridging ligand, and is also coordinated by four N atoms of another ligand. The Mn atom is seven-coordinated in a penta-gonal-bipyramidal environment. The crystal structure displays inter-molecular π-π inter-actions between adjacent pyridine rings, with a shortest centroid-centroid distance of 3.784 (3) Å. The perchlorate is linked to the dinuclear cation by O-H⋯O hydrogen bonds.

| S-EPMC2983616 | biostudies-literature

Bis(μ-N,N'-di-4-pyridylpyridine-2,6-diamine)bis[dimethacrylatocobalt(II)] dihydrate.

Project description:The Co(II) ion in the title complex, [Co(2)(C(4)H(5)O(2))(4)(C(15)H(13)N(5))(2)]·2H(2)O, has a distorted square-planar coordination formed by the bridging bidentate N,N'-di-4-pyridylpyrid-ine-2,6-diamine (dapmp) ligands and two monodentate carboxyl-ate groups from methacrylates. Two dapmp ligands bridge two Co atoms, forming a dinuclear complex arranged around an inversion centre. N-H⋯O and O-H⋯O hydrogen bonds involving the solvent water mol-ecule result in the formation of a three-dimensional network. The aliphatic moiety of one of the methacrylate groups is disordered over two positions with fixed occupancies of 0.67 and 0.33.

| S-EPMC2959996 | biostudies-literature

Thin-film conformal fluorescent SU8-phenylenediamine.

Project description:The SU8 polymer is a negative photoresist widely used to produce high-quality coatings, with controllable thicknesses ranging from nanometers to millimeters, depending on fabrication protocols. Apart from conventional use cases in microelectronics and fluidics, SU8 is quite an attractive platform in nanophotonics. This material, being straightforwardly processed by ultraviolet lithography, is transparent to wavelengths longer than 500 nm. However, introducing fluorescent agents within the SU8 matrix remains a challenge owing to its high hydrophobicity. Here, we develop a process, where colorful quantum dots co-participate in the polymerization process by epoxide amination and become a part of a new fluorescent material - SU8-phenylenediamine. Through comprehensive characterization methods, including XPS and 1H-NMR analyses, we demonstrate that m-PD covalently binds to SU8 epoxy sites with its molecular amine, virtually forming a new material and not just a mixture of two compounds. After characterizing the new strongly fluorescent platform, thin 300 nm films were created on several surfaces, including a conformal coverage of a nanofluidic capillary. This new process provides opportunities to incorporate various functional molecules into optoelectronic devices without the need for multistep deposition and surface functionalization.

| S-EPMC10634436 | biostudies-literature

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