Novel, one bay-substituted perylene bisanhydride (6) and two bay-substituted perylene bisimides (7, 10) have been successfully synthesized with a large and swallow tail type, 2-decyl-1-tetradecanoyl substituents at the bay area (1 and 7 positions). The non-bay-substituted perylene bisimides with the same N-substituents were prepared as model compounds (3, 9) for comparison. Absorption and fluorescence, electrochemical, spectroelectrochemical, morphological properties of the compounds were investigated, and then, density functional theory (DFT) simulations were conducted. The compounds 6, 7 and 10 have shown J-aggregated featureless, very broad absorbance through the UV–vis-NIR region with a strong fluorescence quenching attributed to efficient intramolecular electron transfer from electron donor 2-decyl-1-tetradecanoyl substituent to PDI acceptor and scaffolds allow π–π intermolecular interactions, induced molecular aggregation. The absolute positions of LUMO and HOMO values for 3, 9, 6, 7 and 10 in solutions were −3.91/−6.09 eV, −3.93/−6.08 eV, −4.02/−5.90 eV, −4.02/−5.91 eV and −4.02/−5.97 eV, respectively. The onset reduction potential of compounds 6, 7 and 10 are lower than those of compounds 3 and 9. Similarly, the onset oxidation potential values of the compounds 6, 7 and 10 are smaller than those of the non-bay-substituted perylene dyes 3 and 9. The synthesized compounds (3 with 7; 9 with 10) can be exploited as an off-on fluorescence probes for photonic applications.

新颖，一个托架，取代的苝二酐（6）和两个托架取代的苝二酰亚胺（7，10）已经被成功地与在隔舱区大和燕尾型，2-癸基-1-十四酰基取代基的合成（1和7个职位）。具有相同的N-取代基的非托架取代的二萘嵌苯双酰亚胺制备成模型化合物（3，9用于比较）。研究了化合物的吸收和荧光，电化学，光谱电化学，形态学性质，然后进行了密度泛函理论（DFT）的模拟。化合物6，7和10已显示J聚集在UV-vis-NIR区域无特征，非常宽的吸收，并具有强大的荧光猝灭作用，这归因于分子内电子从电子供体2-癸基-1-十四烷酰基取代基到PDI受体和支架的有效分子内转移，从而使π-π分子间相互作用，诱导分子聚集。LUMO和HOMO值的绝对位置3，9，6，7和10在溶液是-3.91 / -6.09电子伏特，-3.93 / -6.08电子伏特，-4.02 / -5.90电子伏特，-4.02 / -5.91 eV和-分别为4.02 / −5.97 eV。化合物的起始还原电位6，7和10比那些化合物的低3和9。类似地，化合物的起始氧化电势值6，7和10比非托架取代苝的较小染料3和9。合成的化合物（3到7；9到10）可以用作光子学应用的离线荧光探针。