Veale Emma B, Tocci Gillian M, Pfeffer Frederick M, Kruger Paul E, Gunnlaugsson Thorfinnur
School of Chemistry, Centre of Synthesis and Chemical Biology, University of Dublin, Trinity College Dublin, Dublin2, Ireland.
Org Biomol Chem. 2009 Sep 7;7(17):3447-54. doi: 10.1039/b907037k. Epub 2009 Jul 6.
The thiourea based 4-amino-1,8-naphthalimide molecules 1-5 were designed as fluorescent anion sensors and their photophysical properties investigated upon recognition of biologically relevant anions such as acetate, dihydrogen phosphate and fluoride in DMSO. Synthesised in a single step from their respective aniline precursors, 6-9, these molecules were designed on the fluorophore-spacer-receptor principle, where in the case of sensors 1-3 the thiourea anion recognition moieties were connected to the fluorophore via the 4-amino moiety, while sensors 4 and 5 had the thiourea moieties connected to the 'imide' via a CH2 spacer. The current study showed that 1-5 operated as photoinduced electron transfer (PET) sensors, as no significant changes were observed in their absorption spectra, while their fluorescence emissions were quenched upon recognition of ions such as AcO(-), H2PO4(-) and F(-), which demonstrates that bidirectional PET sensing occurs in such naphthalimide based anion sensors.
基于硫脲的4-氨基-1,8-萘二甲酰亚胺分子1-5被设计为荧光阴离子传感器，并研究了它们在二甲基亚砜中识别生物相关阴离子（如醋酸根、磷酸二氢根和氟离子）时的光物理性质。这些分子由各自的苯胺前体6-9一步合成，基于荧光团-间隔基-受体原理设计，其中在传感器1-3的情况下，硫脲阴离子识别部分通过4-氨基部分连接到荧光团，而传感器4和5的硫脲部分通过CH2间隔基连接到“酰亚胺”。当前研究表明，1-5作为光诱导电子转移（PET）传感器起作用，因为在它们的吸收光谱中未观察到显著变化，而在识别诸如AcO(-)、H2PO4(-)和F(-)等离子时它们的荧光发射被猝灭，这表明在这种基于萘二甲酰亚胺的阴离子传感器中发生双向PET传感。
