TY - JOUR
T1 - Interpretable Deep-Learning Unveils Structure-Property Relationships in Polybenzenoid Hydrocarbons
AU - Weiss, Tomer
AU - Wahab, Alexandra
AU - Bronstein, Alex M.
AU - Gershoni-Poranne, Renana
N1 - Publisher Copyright: © 2023 American Chemical Society
PY - 2023/7/21
Y1 - 2023/7/21
N2 - In this work, interpretable deep learning was used to identify structure-property relationships governing the HOMO-LUMO gap and the relative stability of polybenzenoid hydrocarbons (PBHs) using a ring-based graph representation. This representation was combined with a subunit-based perception of PBHs, allowing chemical insights to be presented in terms of intuitive and simple structural motifs. The resulting insights agree with conventional organic chemistry knowledge and electronic structure-based analyses and also reveal new behaviors and identify influential structural motifs. In particular, we evaluated and compared the effects of linear, angular, and branching motifs on these two molecular properties and explored the role of dispersion in mitigating the torsional strain inherent in nonplanar PBHs. Hence, the observed regularities and the proposed analysis contribute to a deeper understanding of the behavior of PBHs and form the foundation for design strategies for new functional PBHs.
AB - In this work, interpretable deep learning was used to identify structure-property relationships governing the HOMO-LUMO gap and the relative stability of polybenzenoid hydrocarbons (PBHs) using a ring-based graph representation. This representation was combined with a subunit-based perception of PBHs, allowing chemical insights to be presented in terms of intuitive and simple structural motifs. The resulting insights agree with conventional organic chemistry knowledge and electronic structure-based analyses and also reveal new behaviors and identify influential structural motifs. In particular, we evaluated and compared the effects of linear, angular, and branching motifs on these two molecular properties and explored the role of dispersion in mitigating the torsional strain inherent in nonplanar PBHs. Hence, the observed regularities and the proposed analysis contribute to a deeper understanding of the behavior of PBHs and form the foundation for design strategies for new functional PBHs.
UR - http://www.scopus.com/inward/record.url?scp=85147149762&partnerID=8YFLogxK
U2 - https://doi.org/10.1021/acs.joc.2c02381
DO - https://doi.org/10.1021/acs.joc.2c02381
M3 - مقالة
SN - 0022-3263
VL - 88
SP - 9645
EP - 9656
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -