期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 24, 页码 9009-9015出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c05172
关键词
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资金
- European Research Council [695009]
- UK Engineering and Physical Sciences Research Council [EPSRC EP/P027067/1]
- Sustainability and Energy Research Initiative (SAERI) foundation at the Weizmann Institute of Science (Israel)
- University of Cambridge
- Cambridge Trusts
- Chinese Scholarship Council
- Royal Society
- ERC [758370]
- EPSRC [EP/L000202, EP/R029431, EP/T022213]
- EPSRC [EP/P027067/1] Funding Source: UKRI
This study demonstrates how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent influences the stereochemical outcome of self-assembly. The presence of methyl groups alters the self-sorting behavior, while the axial chirality of the BINOL building block affects the handedness of the helicate metal center.
Here we demonstrate how the hydrogen-bonding ability of a BINOL-based dialdehyde subcomponent dictated the stereochemical outcome of its subsequent self-assembly into one diastereomeric helicate form when bearing free hydroxy groups, and another in the case of its methylated congener. The presence of methyl groups also altered the self-sorting behavior when mixed with another, short linear dialdehyde subcomponent, switching the outcome of the system from narcissistic to integrative self-sorting. In all cases, the axial chirality of the BINOL building block also dictated helicate metal center handedness during stereospecific self-assembly. A new family of stereochemically pure heteroleptic helicates were thus prepared using the new knowledge gained. We also found that switching from Fe-II to Zn-II, or the incorporation of a longer linear ligand, favored heteroleptic structure formation.
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