PMID- 30855042
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20190322
LR  - 20190322
IS  - 2040-3372 (Electronic)
IS  - 2040-3364 (Linking)
VI  - 11
IP  - 12
DP  - 2019 Mar 21
TI  - Self-assembly of 5,6-dihydroxyindole-2-carboxylic acid: polymorphism of a 
      eumelanin building block on Au(111).
PG  - 5422-5428
LID - 10.1039/c8nr09810g [doi]
AB  - Investigating two-dimensional (2D) self-assembled structures of biological 
      monomers governed by intermolecular interactions is a prerequisite to understand 
      the self-assembly of more complex biomolecular systems. 5,6-Dihydroxyindole 
      carboxylic acid (DHICA) is one of the building blocks of eumelanin - an irregular 
      heteropolymer and the most common form of melanin which has potential 
      applications in organic electronics and bioelectronics. By means of scanning 
      tunneling microscopy, density functional theory and Monte Carlo calculations, we 
      investigate DHICA molecular configurations and interactions underlying the 
      multiple 2D patterns formed on Au(111). While DHICA self-assembled molecular 
      networks (SAMNs) are dominated by the hydrogen bonding of carboxylic acid dimers, 
      a variety of 2D architectures are formed due to the multiple weak interactions of 
      the catechol group. The hydroxyl group also allows for redox reactions, caused by 
      oxidation via O2 exposure, resulting in molecular rearrangement. The 
      susceptibility of the molecules to oxidation is affected by their SAMNs 
      architectures, giving insights on the reactivity of indoles as well as 
      highlighting non-covalent assembly as an approach to guide selective oxidation 
      reactions.
FAU - De Marchi, F
AU  - De Marchi F
AD  - Centre Energie, Materiaux et Telecommunications, Institut National de la 
      Recherche Scientifique, 1650 Boulevard Lionel-Boulet, Varennes, QC, Canada J3X 
      1S2. maryam.ebrahimi@emt.inrs.ca rosei@emt.inrs.ca.
FAU - Galeotti, G
AU  - Galeotti G
FAU - Simenas, M
AU  - Simenas M
FAU - Ji, P
AU  - Ji P
FAU - Chi, L
AU  - Chi L
FAU - Tornau, E E
AU  - Tornau EE
FAU - Pezzella, A
AU  - Pezzella A
FAU - MacLeod, J
AU  - MacLeod J
FAU - Ebrahimi, M
AU  - Ebrahimi M
FAU - Rosei, F
AU  - Rosei F
LA  - eng
PT  - Journal Article
PL  - England
TA  - Nanoscale
JT  - Nanoscale
JID - 101525249
EDAT- 2019/03/12 06:00
MHDA- 2019/03/12 06:01
CRDT- 2019/03/12 06:00
PHST- 2019/03/12 06:00 [pubmed]
PHST- 2019/03/12 06:01 [medline]
PHST- 2019/03/12 06:00 [entrez]
AID - 10.1039/c8nr09810g [doi]
PST - ppublish
SO  - Nanoscale. 2019 Mar 21;11(12):5422-5428. doi: 10.1039/c8nr09810g.