Department of Chemistry, Fordham University, 441 E. Fordham Road, Bronx, NY 10458, USA.
Beilstein J Org Chem. 2013 Oct 31;9:2320-7. doi: 10.3762/bjoc.9.266. eCollection 2013.
Bisimine and bisamine AB2 monomers have been synthesized from 3,5-diaminobenzoic acid and benzaldehyde derivatives without the need for protective groups or purification. This monomer preparation is universal for various electron-donating and electron-withdrawing benzaldehyde substrates. To demonstrate the versatility of these previously unreported AB2 monomers in the formation of high molecular weight structures, novel first-generation dendrimers and hybrid second-generation dendrimers have been synthesized. Using fluorescence spectroscopy, pyrene was shown to be removed from an aqueous environment upon exposure to thin dendrimer films, with the first-generation dendrimer removing 70% of the pyrene within 30 min and the hybrid second-generation dendrimers removing 38-52%. Inclusion formation constants were calculated to be on the order of 10(9)-10(11) M(-1) and are comparable to the values of previously reported macromolecules. These results illustrate that size may not influence pyrene removal as effectively as composition.
已成功地从 3,5-二氨基苯甲酸和苯甲醛衍生物合成了双亚胺和双亚胺 AB2 单体，无需使用保护基团或进行纯化。这种单体的制备方法适用于各种供电子和吸电子苯甲醛底物。为了证明这些之前未报道过的 AB2 单体在形成高分子量结构方面的通用性，已经合成了新型第一代树状大分子和混合第二代树状大分子。通过荧光光谱法，发现在暴露于薄的树状大分子膜时，芘会从水相环境中被去除，其中第一代树状大分子在 30 分钟内去除了 70%的芘，而混合第二代树状大分子则去除了 38-52%。包合形成常数的计算值为 10(9)-10(11) M(-1)，与之前报道的大分子相当。这些结果表明，大小可能不像组成那样有效地影响芘的去除。
