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Title: Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study

Abstract

For this study, the self-assembly properties of N(9)-(2,3-dihydroxypropyl adenine) (DHPA), a plausible prebiotic nucleoside analogue of adenosine, were investigated using density functional theory. Two different isomers were considered, and it is found that while both isomers can form a variety of structures, including chains, one of them is also able to form cages and helixes. When these results were put in the context of substrate supported molecular self-assembly, it is concluded that gas-phase self-assembly studies that consider isomer identity and composition not only can aid interpreting the experimental results, but also reveal structures that might be overlooked otherwise. In particular, this study suggest that a double-helical structure made of DHPA molecules which could have implications in prebiotic chemistry and nanotechnology, is stable even at room temperature. For example electrical properties (energy gap of 4.52eV) and a giant permanent electrical dipole moment (49.22 Debye) were found in our larger double-helical structure (3.7 nm) formed by 14 DHPA molecules. Lastly, the former properties could be convenient for construction of organic dielectric-based devices.

Authors:
 [1];  [2];  [2];  [1]
  1. Escuela Superior de Apan, Universidad Autonoma del Estado de Hidalgo (Mexico)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS) and Computer Science and Mathematics Division
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1341529
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
International Journal of Quantum Chemistry
Additional Journal Information:
Journal Volume: 117; Journal Issue: 3; Journal ID: ISSN 0020-7608
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE

Citation Formats

Vallejo, Emmanuel, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., and Rangel Cortes, Eduardo. Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study. United States: N. p., 2016. Web. doi:10.1002/qua.25314.
Vallejo, Emmanuel, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., & Rangel Cortes, Eduardo. Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study. United States. doi:10.1002/qua.25314.
Vallejo, Emmanuel, Fuentes-Cabrera, Miguel, Sumpter, Bobby G., and Rangel Cortes, Eduardo. Sat . "Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study". United States. doi:10.1002/qua.25314. https://www.osti.gov/servlets/purl/1341529.
@article{osti_1341529,
title = {Isomeric effects on the self-assembly of a plausible prebiotic nucleoside analogue: A theoretical study},
author = {Vallejo, Emmanuel and Fuentes-Cabrera, Miguel and Sumpter, Bobby G. and Rangel Cortes, Eduardo},
abstractNote = {For this study, the self-assembly properties of N(9)-(2,3-dihydroxypropyl adenine) (DHPA), a plausible prebiotic nucleoside analogue of adenosine, were investigated using density functional theory. Two different isomers were considered, and it is found that while both isomers can form a variety of structures, including chains, one of them is also able to form cages and helixes. When these results were put in the context of substrate supported molecular self-assembly, it is concluded that gas-phase self-assembly studies that consider isomer identity and composition not only can aid interpreting the experimental results, but also reveal structures that might be overlooked otherwise. In particular, this study suggest that a double-helical structure made of DHPA molecules which could have implications in prebiotic chemistry and nanotechnology, is stable even at room temperature. For example electrical properties (energy gap of 4.52eV) and a giant permanent electrical dipole moment (49.22 Debye) were found in our larger double-helical structure (3.7 nm) formed by 14 DHPA molecules. Lastly, the former properties could be convenient for construction of organic dielectric-based devices.},
doi = {10.1002/qua.25314},
journal = {International Journal of Quantum Chemistry},
number = 3,
volume = 117,
place = {United States},
year = {2016},
month = {10}
}

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Works referenced in this record:

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Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
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