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Theoretical Design of Bioinspired Macromolecular Electrets Based on Anthranilamide Derivatives

机译：基于邻氨基苯甲酰胺衍生物的生物启发高分子驻极体的理论设计

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Polypeptide helices possess considerable intrinsic dipole moments oriented along their axes. While for proline helices the dipoles originate solely from the ordered orientation of the amide bonds,for 3_(10-) and α-helices the polarization resultant from the formation of hydrogen-bond network further increases the magnitude of the macromolecular dipoles. The enormous electric-field gradients,generated by the dipoles of α-helices (which amount to about 5 D per residue with 0.15 nm residue increments along the helix),play a crucial role in the selectivity and the transport properties of ion channels. The demonstration of dipole-induced rectification of vectorial charge transfer mediated by α-helices has opened a range of possibilities for applications of these macromolecules in molecular and biomolecular electronics. These biopolymers,however,possess relatively large bandgaps. As an alternative,we examined a series of synthetic macromolecules,aromatic oligo-ortho-amides,which form extended structures with amide bonds in ordered orientation,supported by a hydrogen-bond network. Unlike their biomolecular counterparts,the extended n-conjugation of these macromolecules will produce bandgaps significantly smaller than the polypeptide bandgaps. Using ab initio density functional theory calculations,we modeled anthranilamide derivatives that are representative oligo-ortho-amide conjugates. Our calculations,indeed,showed intrinsic dipole moments oriented along the polymer axes and increasing with the increase in the length of the oligomers. Each anthranilamide residue contributed about 3 D to the vectorial macromolecular dipole. When we added electron donating (diethylamine) and electron withdrawing (nitro and trifluoromethyl) groups for n- and p-doping,respectively,we observed that: (1) proper positioning of the electron donating and withdrawing groups further polarized the aromatic residues,increasing the intrinsic dipole to about 4.5 D per residue; and (2) extension of the n-conjugation over some of the doping groups narrowed the band gaps with as much as 1 eV. The investigated bioinspired systems offer alternatives for the development of broad range of organic electronic materials with nonlinear properties.
机译：多肽螺旋具有许多沿其轴取向的固有偶极矩。对于脯氨酸螺旋而言，偶极子仅源于酰胺键的有序取向，而对于3_（10-）和α螺旋，由于氢键网络的形成而产生的极化进一步增加了大分子偶极子的大小。 α螺旋偶极子所产生的巨大电场梯度（每个残基大约为5 D，沿着螺旋的残基增量为0.15 nm）在离子通道的选择性和传输特性中起着至关重要的作用。由α螺旋介导的偶极诱导的矢量电荷转移整流的演示为这些大分子在分子和生物分子电子学中的应用打开了一系列可能性。但是，这些生物聚合物具有较大的带隙。作为替代方案，我们研究了一系列合成的大分子芳香族低聚原酰胺，它们形成了具有氢键网络支持的有序取向的酰胺键的扩展结构。与它们的生物分子对应物不同，这些大分子的扩展n共轭作用将产生明显小于多肽带隙的带隙。使用从头算密度泛函理论计算，我们模拟了代表低聚正酰胺结合物的邻氨基苯甲酰胺衍生物。实际上，我们的计算显示了固有的偶极矩沿着聚合物轴取向，并随着低聚物长度的增加而增加。每个蒽酰胺残基对向量大分子偶极贡献约3D。当我们分别添加供电子基团（二乙胺）和吸电子基团（硝基和三氟甲基）时，我们观察到：（1）供电电子基团和吸电子基团的正确定位进一步使芳香族残基极化，从而增加本征偶极子至每个残基约4.5 D; （2）在某些掺杂基团上扩展了n共轭，使带隙缩小了1 eV。经过研究的受生物启发的系统为开发具有非线性特性的各种有机电子材料提供了替代方案。

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