TY - JOUR
T1 - Unravelling supramolecular photocycloaddition
T2 - Cavitand-mediated reactivity of 3-(Aryl)Acrylic acids
AU - Kashyap, Akshay
AU - Balraj, Vasu
AU - Ramalingam, Vijayakumar
AU - Pattabiraman, Mahesh
N1 - Funding Information:
This work was financially supported by National Institute of General Medical Science of the National Institutes of Health (NIH) under award number GM103427. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. MP thanks the NE-DED (Contract# 20-01-030) and Shabri LLC for the use of instruments in this project purchased through Academic R&D Grant.
Funding Information:
This work was financially supported by National Institute of General Medical Science of the National Institutes of Health (NIH) under award number GM103427. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. MP thanks the NE-DED (Contract# 20-01-030) and Shabri LLC for the use of instruments in this project purchased through Academic R&D Grant.
Publisher Copyright:
© 2021 Elsevier B.V.
PY - 2022/3/1
Y1 - 2022/3/1
N2 - The supramolecular photocycloaddition (PCA) of 3-(phenyl)acrylic acid has been extensively pursued by chemists to study weak interactions and synthesize substituted cyclobutanes. The stereo- and regioselectivity of the products in a supramolecularly affected reaction are often used as a probe for assessing the nature of weak interactions and/or molecular ambience of the reactants. However, some crucial aspects of this chemistry have often remained underexplored in the past, especially within the context of interpreting strength and directionality of interactions based on reaction outcomes. We present a detailed study of the cavitand-mediated PCA of a new and suitable reactant (3-(naphthyl)acrylic acids) that exhibits labile photo-reversible chemistry, which is suitable for exploring previously unexplored aspects of the supramolecular PCA chemistry. Our studies afford important insights about this chemistry that should be considered while using product selectivity as a proxy for deducing intermolecular interactions.
AB - The supramolecular photocycloaddition (PCA) of 3-(phenyl)acrylic acid has been extensively pursued by chemists to study weak interactions and synthesize substituted cyclobutanes. The stereo- and regioselectivity of the products in a supramolecularly affected reaction are often used as a probe for assessing the nature of weak interactions and/or molecular ambience of the reactants. However, some crucial aspects of this chemistry have often remained underexplored in the past, especially within the context of interpreting strength and directionality of interactions based on reaction outcomes. We present a detailed study of the cavitand-mediated PCA of a new and suitable reactant (3-(naphthyl)acrylic acids) that exhibits labile photo-reversible chemistry, which is suitable for exploring previously unexplored aspects of the supramolecular PCA chemistry. Our studies afford important insights about this chemistry that should be considered while using product selectivity as a proxy for deducing intermolecular interactions.
KW - Cucurbituril
KW - Cyclodextrin
KW - Host-guest chemistry
KW - Photocycloaddition
KW - Supramolecular chemistry
KW - Truxillic acid
KW - Truxinic acid
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U2 - 10.1016/j.jphotochem.2021.113695
DO - 10.1016/j.jphotochem.2021.113695
M3 - Article
C2 - 35340561
AN - SCOPUS:85120641627
SN - 1010-6030
VL - 425
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
M1 - 113695
ER -