Selective Isolation of Polycyclic Aromatic Hydrocarbons
by Self-Assembly of a Tunable N→B Clathrate
Angel
D. Herrera-España
Gonzalo Campillo-Alvarado
Perla Román-Bravo
Dea Herrera-Ruiz
Herbert Höpfl
Hugo Morales-Rojas
10.1021/acs.cgd.5b00219.s001
https://acs.figshare.com/articles/journal_contribution/Selective_Isolation_of_Polycyclic_Aromatic_Hydrocarbons_by_Self_Assembly_of_a_Tunable_N_B_Clathrate/2181865
The combination of one dipyridyl
linker [1,2-di(4-pyridyl)ethylene
(DPE), 1,2-di(4-pyridyl)ethane (DPEt), or 4,4′-azopyridine
(DPA)] with two molecules of arylboronate ester <b>1</b> produced
dinuclear Lewis-type N→B adducts that can act as acyclic host
for polycyclic aromatic hydrocarbons (PAHs) in the solid state. Nine
crystalline solids of composition PAH@adduct (i.e., one PAH per adduct)
were obtained from solutions containing a single PAH. On the basis
of the single-crystal X-ray diffraction analysis of the compound ANT@A1
(ANT = anthracene; A1 = adduct being composed of DPE and two boronate
esters <b>1</b>), the PAH inclusion selectivity is related to
a size-fitting adaptation to an octaedral-shaped pocket assembled
by CH-π interactions between fragments of the diamine and the
arylboronate ester <b>1</b>. The resulting reversible organic
clathrates can perform “catch and release” cycles of
PAHs such as pyrene and can sequester selectively PAHs from mixtures
in solution.
2015-04-01 00:00:00
arylboronate ester 1
PAH inclusion selectivity
arylboronate ester 1.
Selective Isolation
acyclic host
adduct
CH
DPE
DPA
Polycyclic Aromatic Hydrocarbons