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Syntheses, X‐Ray Crystal Structures, Emission Properties and DFT Calculations of Monoprotonated Polypyridines
Author(s) -
Yoshikawa Naokazu,
Yamazaki Shoko,
Kato Natsumi,
Kubota Akari,
Sawai Mika,
Noda Kaoru,
Kanehisa Nobuko,
Inoue Tsuyoshi,
Nakata Eiji,
Takashima Hiroshi
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802830
Subject(s) - chemistry , planarity testing , pyridine , acetonitrile , hydrogen bond , ring (chemistry) , nitrogen , proton , density functional theory , quantum yield , hydrogen , crystal structure , crystallography , photochemistry , computational chemistry , molecule , medicinal chemistry , organic chemistry , fluorescence , physics , quantum mechanics
Abstract Monoprotonated compounds [(L)HPF 6 ] were prepared by the reaction of (L=bpy, phen, dpphen, bqn and ppy) with concentrated HCl in water. Monoprotonated pyridine rings are hydrogen bonded intramolecularly to the adjacent pyridine ring and intermolecularly to the adjacent PF 6 − in compounds. These hydrogen bonds restrain the nonradiative decay to produce intense emission. Density functional theory was applied to interpret the planarity in compounds. The attachment of one proton to the nitrogen in [(dpphen)HPF 6 ] and [(bqn)HPF 6 ] leads to the strong emission in acetonitrile ( Φ = 0.046 and 0.097, respectively). In particular, the attachment of one proton to the ppy nitrogen results in exhibiting a strong emission with a large quantum yield ( Φ = 0.264).