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Absorption spectra of calix[3]pyrrole analogs as probes for contracted macrocycles

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Title: Absorption spectra of calix[3]pyrrole analogs as probes for contracted macrocycles
Authors: Watanabe, Keita Browse this author
Saha, Ranajit Browse this author
Inaba, Yuya Browse this author
Manabe, Yumehiro Browse this author
Yoneda, Tomoki Browse this author →KAKEN DB
Ide, Yuki Browse this author →KAKEN DB
Hijikata, Yuh Browse this author →KAKEN DB
Inokuma, Yasuhide Browse this author →KAKEN DB
Keywords: Calixpyrrole
UV-vis absorption
strained macrocycle
Issue Date: Jan-2023
Publisher: World Scientific Publishing
Journal Title: Journal of porphyrins and phthalocyanines
Volume: 27
Issue: 01n04
Start Page: 157
End Page: 163
Publisher DOI: 10.1142/S1088424622500754
Abstract: Calix[3]pyrrole and its furan derivatives exhibited bathochromically shifted lowest-energy electronic transition bands in their absorption spectra compared with their calix[4]- and calix[6]-pyrrole analogues, despite the repeating units being the same. We also observed fluorescence emission for calix[3]-type macrocycles. The Stokes shift of the furan/pyrrole hybrid macrocycles, calix[2]furan[1]-pyrrole, and calix[1]furan[2]pyrrole, substantially varied depending on the solvent polarity. Non-covalent interaction (NCI) analyses indicated enhanced interactions between neighboring aromatic rings in the calix[3]pyrrole macrocycle, whereas such interactions were weak in calix[4]pyrrole, in which the interchromophore distance is remarkably longer than in calix[3]pyrrole. Theoretical analyses indicated that the red-shifted, lowest-energy bands of calix[3]pyrrole correspond to HOMO-LUMO transitions, the energy gap of which was narrow compared with calix[4]pyrroles. The characteristic absorption bands for calix[3]pyrrole and its related macrocycles are useful as probes for distinguishing such macrocycles from higher calix[n]pyrrole (n & GE; 4) analogues that exhibit almost identical absorption spectra.
Rights: Electronic version of an article published as [Journal, Volume, Issue, Year, Pages] [Article DOI] © [copyright World Scientific Publishing Company] [Journal URL]
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 猪熊 泰英

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