期刊
MOLECULES
卷 25, 期 4, 页码 -出版社
MDPI
DOI: 10.3390/molecules25040907
关键词
cocrystal; crystal engineering; halogen bonding; photodimerization; cyclobutane; pedal motion
资金
- National Science Foundation [LRM DMR-1708673]
The halogen-bond (X-bond) donors 1,3- and 1,4-diiodotetrafluorobenzene (1,3-di-I-tFb and 1,4-di-I-tFb, respectively) form cocrystals with trans-1,2-bis(2-pyridyl)ethylene (2,2'-bpe) assembled by N center dot center dot center dot I X-bonds. In each cocrystal, 2(1,3-di-I-tFb)center dot 2(2,2'-bpe) and (1,4-di-I-tFb)center dot(2,2'-bpe), the donor molecules support the C=C bonds of 2,2'-bpe to undergo an intermolecular [2+2] photodimerization. UV irradiation of each cocrystal resulted in stereospecific and quantitative conversion of 2,2'-bpe to rctt-tetrakis(2-pyridyl)cyclobutane (2,2'-tpcb). In each case, the reactivity occurs via face-to-face pi-stacked columns wherein nearest-neighbor pairs of 2,2'-bpe molecules lie sandwiched between X-bond donor molecules. Nearest-neighbor C=C bonds are stacked criss-crossed in both cocrystals. The reactivity was ascribed to the olefins undergoing pedal-like motion in the solid state. The stereochemistry of 2,2'-tpcb is confirmed in cocrystals 2(1,3-di-I-tFb)center dot(2,2'-tpcb) and (1,4-di-I-tFb)center dot(2,2'-tpcb).
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