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Electrogenerated Chemiluminescence of a BODIPY Derivative with Extended Conjugation
Author(s) -
Ishimatsu Ryoichi,
Shintaku Hirosato,
Adachi Chihaya,
Nakano Koji,
Imato Toshihiko
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702449
Subject(s) - derivative (finance) , bodipy , chemistry , photochemistry , stokes shift , chemiluminescence , electrochemiluminescence , singlet state , electrochemistry , ion , excited state , annihilation , fluorescence , luminescence , electrode , materials science , organic chemistry , atomic physics , physics , financial economics , economics , optoelectronics , quantum mechanics
The electrochemical properties and electrogenerated chemiluminescence (ECL) of a borondipyrromethane (BODIPY) derivative, 2,8‐bis(4‐isopropylphenyl)‐difuro[2, 3‐ b ][3, 2‐ g ]‐5,5‐difluoro‐5‐bora‐3a,4a‐diaza‐ s ‐indacene (Derivative 1, Figure 1) are described. Derivative 1 emitted ECL in the range of 650∼800 nm by using tripropylamine (TPA) as a coreactant. In the cyclic voltammogram, Derivative 1 showed a reversible oxidation wave, whereas the reduction wave was irreversible. Energetically, it is likely that triplet‐triplet annihilation is the main pathway to emit ECL through the ion annihilation of the radical anions and cations of Derivative 1 whereas the lowest excited singlet state of Derivative 1 is directly produced with TPA. The maximum ECL wavelengths (670 nm at 0.01 mM) were red‐shifted with increasing the concentration of Derivative 1 because of the self‐absorption resulted from a small Stokes shift (∼10 nm). Relative ECL efficiency of Derivative 1 was 0.13 compared to that of a Ru(bpy) 2+ /TPA system.