12.3.2 Cationic Water-Soluble 44CBP3
Yu et al. demonstrated cationic water-soluble 4,4
0 -biphen[3]arene (44CBP3TM) with six quaternary ammonium groups (Scheme 8) [42]. The precursor
44BP3-Br, containing six alkyl bromide terminal groups, was prepared through
the cyclization of monomer with para-formaldehyde in 1,2-dichloroethane in
the presence of BF 3 O(Et) 2 catalyst. It was easily functionalized to generate
water-soluble 44CBP3-TM by treating 44BP3-Br with excess trimethylamine
in methanol. Meanwhile, the self-assembly behavior of 44CBP3-TM was
investigated.
12.3.3 Anionic Water-Soluble 22BP4
Besides the above-mentioned water-soluble 4,4
0 -biphen[n]arene, a water-soluble
2,2
0 -biphen[n]arene (22CBP4) containing eight carboxylato moieties was synthesized by our group (Scheme 9) using a similar synthetic procedure of 44CBP3 and
44CBP4 [43]. 22CBP4 has a very good solubility (!10 mM) in water. In addition,
the first example of complexation of biological and pharmaceutical molecules by
22CBP4 in water was investigated (Table 1).
Scheme 7 Synthesis of the anionic water-soluble 4,4
0 -biphen[3,4]arene [39–41]
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B. Li et al.
Yu et al. demonstrated cationic water-soluble 4,4
0 -biphen[3]arene (44CBP3TM) with six quaternary ammonium groups (Scheme 8) [42]. The precursor
44BP3-Br, containing six alkyl bromide terminal groups, was prepared through
the cyclization of monomer with para-formaldehyde in 1,2-dichloroethane in
the presence of BF 3 O(Et) 2 catalyst. It was easily functionalized to generate
water-soluble 44CBP3-TM by treating 44BP3-Br with excess trimethylamine
in methanol. Meanwhile, the self-assembly behavior of 44CBP3-TM was
investigated.
12.3.3 Anionic Water-Soluble 22BP4
Besides the above-mentioned water-soluble 4,4
0 -biphen[n]arene, a water-soluble
2,2
0 -biphen[n]arene (22CBP4) containing eight carboxylato moieties was synthesized by our group (Scheme 9) using a similar synthetic procedure of 44CBP3 and
44CBP4 [43]. 22CBP4 has a very good solubility (!10 mM) in water. In addition,
the first example of complexation of biological and pharmaceutical molecules by
22CBP4 in water was investigated (Table 1).
Scheme 7 Synthesis of the anionic water-soluble 4,4
0 -biphen[3,4]arene [39–41]
318
B. Li et al.