Abstract
A new pair of 2,2ʹ-diamino-1,1ʹ-binaphthyl linked porphyrin dimers, (R)-/(S)-H, were synthesized to study their supramolecular interactions with a pair of chiral diamines ((R)-/(S)-PPDA) by using UV-Vis absorption, fluorescence and NMR titrations. The spectroscopic titrations indicated that sandwich-type 1:1 complexes were formed at low guest concentration and then transformed to 1:2 open complexes at high guest concentration. The supramolecular interactions afforded sensitive circular dichroism responses, and the CD signs of the 1:1 complexes are decided by the stereostructure of chiral diamine guests. Moreover, due to the shortened linking units, (R)-/(S)-H show more sensitive and predicable CD response than the previously reported hosts (R)-/(S)-H1 and this can be reasonably explained by DFT molecular modeling. The present results suggest (R)-/(S)-H are promising for chiral optical sensing.
Highlights
Chiral phenomenon widely exists in nature such as proteins, polysaccharides and nucleic acids, playing an important role in the development and evolution of life
We reported 1,1′-bi-2-naphthol (BINOL) linked porphyrin dimers for the study of intermolecular chirality modulation and chiral discrimination toward a range of model diamines (Lu et al, 2017a)
The sandwich complexes were found stable up to 67 equiv of (R)-/(S)-PPDA were added, and the association constants (Kassoc) of (R)-HI(S)-PPDA and (R)-HI(R)PPDA were evaluated as 3.87 × 104 M−1 and 2.88 × 104 M−1, respectively (Thordarson, 2011)
Summary
Chiral phenomenon widely exists in nature such as proteins, polysaccharides and nucleic acids, playing an important role in the development and evolution of life. The structures of 1,1ʹ-binaphthyl derivatives are highly tunable since the 2-, 3-, 4-, 6-, 7-, 8- and 9-positions can be systematically modified by introducing functional groups. As a result, they have found extensive applications in the development of optoelectric materials (Yu et al, 2011), optical sensors for molecular recognition (Yu et al, 2013) and asymmetric catalysis (Chen et al, 2003). Significance for the development of chiral discrimination systems In this respect, we reported 1,1′-bi-2-naphthol (BINOL) linked porphyrin dimers for the study of intermolecular chirality modulation and chiral discrimination toward a range of model diamines (Lu et al, 2017a). The importance of the linking units in bisporphyrin hosts for chiral recognition was revealed by comparing with the previously reported hosts (R)-/(S)-H1 (Lu et al, 2017b)
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
