The cis configuration of amino-modified tetraphenylethene for selective detection of single-stranded guanine-rich DNA

Abstract

The selectivity and sensitivity of amino-functionalized tetraphenylethene probes (namely Z-N2TPE and E-N2TPE) for ssDNA detection in aqueous solution were investigated. Both Z-N2TPE and E-N2TPE showed high selectivity to guanine-rich ssDNA. The sensitivity was found to be positively related to the DNA length, indicating the longer DNA could binding more probes to cause aggregation induced fluorescence. Z-N2TPE and E-N2TPE could detect guanine-rich ssDNA as short as 5 nt and 10 nt respectively. Theoretical simulation calculation shows that the amino group of the probe could simultaneously bind with guanine and phosphate ester, which contribute to high selectivity. And the cis probe could bind DNA with higher affinity than the trans one, since the two amino groups of Z-N2TPE could synergistically bind DNA while E-N2TPE could bind DNA with only one amino group.