5,6,12,13‐Tetraazaperopyrenes with different number of tert‐butyl groups (c‐TAPP‐T, c‐TAPP‐H) were synthesized, via four‐fold Bischler–Napieralski cyclization as the key step. As deduced from the single‐crystal structures and optical properties, N‐doping and substitution type allow for a precise control of intermolecular interactions. Compared to the reported 1,3,8,10‐tetraazaperopyrenes, significantly different packing modes were found in 5,6,12,13‐tetraazaperopyrenes. Going from c‐TAPP‐T to c‐TAPP‐H, two additional tert‐butyl groups lead to different preferential growth directions, affording 1D and 2D microcrystals, respectively. Most importantly, both microcrystals exhibit excellent optical waveguide properties with extraordinarily low loss coefficients and unique polarization features. Although c‐TAPP‐H possesses a rigid and planar core, its crystals display an exceptional mechanochromic fluorescence, which, again, depends on the mode of molecular packing.

中文翻译：

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5,6,12,13-四氮杂戊并吡咯是独特的光子和机械变色荧光团。

通过四倍的Bischler-Napieralski环化反应作为关键步骤，合成了具有不同叔丁基数量（c-TAPP-T，c-TAPP-H）的5,6,12,13-四氮杂戊并戊烯。从单晶结构和光学性质推论，N掺杂和取代类型可以精确控制分子间的相互作用。与已报道的1,3,8,10-四氮杂戊py烯相比，在5,6,12,13-四氮杂ap庚烯中发现了明显不同的包装方式。从c-TAPP-T到c-TAPP-H，另外两个叔丁基导致不同的优先生长方向，分别提供1D和2D微晶。最重要的是，两种微晶均具有出色的光波导特性，极低的损耗系数和独特的偏振特性。尽管c‐TAPP‐H具有刚性且平坦的核心，