TY - JOUR
T1 - A new fluorogenic sensing platform for salicylic acid derivatives based on π-π and NH-π interactions between electron-deficient and electron-rich aromatics
AU - Pandith, Anup
AU - Hazra, Giridhari
AU - Kim, Hong Seok
N1 - Funding Information:
This research was supported by the Basic Science Research Program of the National Research Foundation of Korea (NRF) funded by Republic of Korea (2013R1A1A2006777).
Publisher Copyright:
© 2017 Elsevier B.V.
PY - 2017/5/5
Y1 - 2017/5/5
N2 - A novel simple fluorescent probe was designed for the recognition of electron-rich salicylic acid derivatives (SAs). The imidazole-appended aminomethyl perylene probe 1 selectively differentiated between electron-rich amino-SAs and electron-deficient nitro-SAs in EtOH, exhibiting the highest selectivity and sensitivity toward 5-aminosalicylic acid (5-ASA) and showing strong 1:1 binding (Ka = 1.37 × 107 M− 1). This high selectivity and sensitivity resulted from the synergistic multiple hydrogen bonding interactions of secondary amine and imidazole units and π-π interactions between electron-rich and electron-deficient rings, along with the unusual NH-π interactions between 5-ASA and the perylene moiety of 1. The limit of detection (LOD) for 5-ASA in EtOH was 0.012 ppb.
AB - A novel simple fluorescent probe was designed for the recognition of electron-rich salicylic acid derivatives (SAs). The imidazole-appended aminomethyl perylene probe 1 selectively differentiated between electron-rich amino-SAs and electron-deficient nitro-SAs in EtOH, exhibiting the highest selectivity and sensitivity toward 5-aminosalicylic acid (5-ASA) and showing strong 1:1 binding (Ka = 1.37 × 107 M− 1). This high selectivity and sensitivity resulted from the synergistic multiple hydrogen bonding interactions of secondary amine and imidazole units and π-π interactions between electron-rich and electron-deficient rings, along with the unusual NH-π interactions between 5-ASA and the perylene moiety of 1. The limit of detection (LOD) for 5-ASA in EtOH was 0.012 ppb.
KW - 5-Aminosalicylic acid
KW - Multiple hydrogen bonding
KW - Perylene
KW - π-π and NH-π interactions
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U2 - 10.1016/j.saa.2017.01.053
DO - 10.1016/j.saa.2017.01.053
M3 - Article
C2 - 28182985
AN - SCOPUS:85011601679
SN - 1386-1425
VL - 178
SP - 151
EP - 159
JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
ER -