Polydopamine and eumelanin models in various oxidation states

Chen, Chun-Teh; Buehler, Markus J.

doi:10.1039/c8cp05037f

Cited by 28 publications

(46 citation statements)

References 41 publications

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“…Proposed structures of PDA without satisfactory experimental confirmation or experimental and computational disproval. [20,15] Cyclic indole tetramers were found in eumelanins formed by oxidative polymerization of DHI. [15] Scheme 10) [21] and dopamine quinone [14] are formed in the initial steps (Scheme 10).…”

Section: Structure and Properties Of Pdamentioning

confidence: 99%

Chemistry of Polydopamine – Scope, Variation, and Limitation

2019

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Polydopamine (PDA) is a polymer easily obtained by oxidation of dopamine. It is composed of indole and dopamine units in various oxidation states and to a lesser extent of pyrroles. It adheres to all type of surfaces even under water due to its abundant catechol moieties assisted by amino groups. This property together with a widespread reactivity to nucleophiles and electrophiles allowing linkage of a variety of entities renders PDA extremely interesting for various applications in biology, biomedicine, membranes, catalysis, materials and water purification. The field of PDA is violently developing. The present review gives an overview about the chemistry and properties of PDA and its analogues with the focus on recent publications. Their widespread applications are occasionally touched. Analogues are obtained by two strategies: post‐modification of PDA and oxidative polymerization of dopamine analogues. Scope and limitations of these strategies are worked out giving impulses for future research in the field.

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Section: Structure and Properties Of Pdamentioning

confidence: 99%

Chemistry of Polydopamine – Scope, Variation, and Limitation

2019

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“…Based on ab initio [35]. This assumption of tetrameric dopamine based structures [36][37][38] as building blocks of PDA is however heavily debated [39] and additional experimental proofs are required.…”

Section: Polydopamine As a Eumelanin Analoguementioning

confidence: 99%

Polydopamine as a stable and functional nanomaterial

Yakhlifi

Ball

2020

Colloids and Surfaces B: Biointerfaces

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The mussel inspired chemistry of dopamine leading to versatile coatings on the surface of all kinds of materials in a one pot process was considered as the unique aspect of catecholamine for a long time. Only recently, research has been undertaken to valorize the simultaneous oxidation and colloid formation in dopamine solutions in the presence of an oxidant. This mini review summarizes the synthesis methods allowing to get controlled nanomaterials, either nanoparticles, hollow capsules or nanotubes and even chiral nanomaterials from dopamine solutions. Finally the applications of those nanomaterials will be described.

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“…Computationally, the structural diversity of DHI oligomers has been recently studied in depth in two publications that have considered a total of more than 45000 structures (dimers up to tetramers) composed by the reduced DHI [13] and the oxidized indolequinone (IQ) and quinone methide (MQ) fragments. [14] Some connectivity and oxidation patterns were excluded a priori on the basis of stability arguments, and the large number of compounds remaining even after these constraints are applied gives an idea of the scale of the problem. These studies have yielded a set of representative oligomer models and provided important insights into the relationship between structure and stability, such as the preference for planar structures, the predominance of IQ fragments in the oxidized oligomers, and the favorable formation, from the energetic point of view, of macrocyclic tetramers.…”

Section: Introductionmentioning

confidence: 99%

Stability and Optical Absorption of a Comprehensive Virtual Library of Minimal Eumelanin Oligomer Models**

Wang

Blancafort

2021

Angewandte Chemie

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Eumelanin is responsible for photoprotection in living organisms. It is made of 5,6-dihydroxyindole (DHI) oligomers. However, lack of detailed structural knowledge limits understanding its function and exploiting its potential in material science. To uncover the relationship between structural stability and optical properties, we have studied a virtual library of minimal oligomer models made of 830 DHI dimers. We find a preference for oxidized, polycyclic structures which speaks in favor of graphite-like structures for the larger oligomers, and propose an electrocyclic formation mechanism. Besides widely considered quinone oxidation patterns, also structures with one or three oxidized sites per fragment and an interfragment double bond are stable, and we introduce a new representative set of 49 stable dimers that considers this diversity. Some stable oxidized dimers have absorption energies as low as 1.3 eV. They may be present as substructures in the naturally found oligomers and contribute to the absorption spectrum of the biopolymer.

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Polydopamine and eumelanin models in various oxidation states

Abstract: The most stable molecular structures of PDA and eumelanin are proposed.

Cited by 28 publications

References 41 publications

Chemistry of Polydopamine – Scope, Variation, and Limitation

Chemistry of Polydopamine – Scope, Variation, and Limitation

Polydopamine as a stable and functional nanomaterial

Stability and Optical Absorption of a Comprehensive Virtual Library of Minimal Eumelanin Oligomer Models**

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