Highly Ordered Phenanthroline-Fused Azaacene

被引：15

作者：

An, Cunbin ^{[1
]}

Guo, Xin ^{[1
]}

Baumgarten, Martin ^{[1
]}

机构：

[1] Max Planck Inst Polymer Res, Polymer Res, D-55128 Mainz, Rhineland Palat, Germany

来源：

CRYSTAL GROWTH & DESIGN | 2015年 / 15卷 / 11期

关键词：

PHYSICAL-PROPERTIES; N-HETEROPENTACENES; NITROGEN; ACENES; DERIVATIVES; PENTACENE; BEHAVIOR; POLYMER;

D O I：

10.1021/acs.cgd.5b00701

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new synthetic route to prepare a centrosymmetric phenanthroline-fused azaacene derivative, TIPS-BisPhNPQ is described. Another axialsymmetric analogue, TIPS-PhNTQ is also synthesized for comparison. Cyclic voltammetry measurements indicate high electron affinity values of -4.03 and -4.01 eV for TIPS-PhNTQ and TIPS-BisPhNPQ respectively. Single-crystal X-ray diffraction reveals that TIPS-PhNTQ forms dimers by intermolecular S-N and N-N interaction, while TIPS-BisPhNPQ shows a highly ordered arrangement via two-dimensional brickwork packing and intermolecular hydrogen bonding. The synthetic protocol established in this paper should be highly applicable to the preparation of more azaacene derivatives with extended pi-conjugations.

引用

页码：5240 / 5245

页数：6

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