A new method for the synthesis of the pentacyclic triphenodioxazines (TPDOs) involving condensation of 6,8-di-(tert-butyl)-3H-phenoxazin-3-one with o-aminophenols has been suggested and a series of sterically crowded 2,4-di-(tert-butyl)-benzo[5,6][1,4]oxazino[2,3-b]phenoxazines (TPDOs) 4 has been prepared. The compounds are well soluble in nonpolar and polar solvents, absorb in the strongest emissive part of the solar spectrum, display intense fluorescence and are characterized by excellent photostability at air conditions. X-ray diffraction study reveals planar structures of heteropentacene cores TPDOs and π-π stacking of the molecules of some of them in crystal. The energy levels of the frontier MOs of the studied TPDOs assessed using the electrochemical methodology and calculated by the DFT B3LYP/6–311++G(d,p) method lie outside the energy domain confined by TiO₂ conductivity zone and redox-mediator I⁻/I₃⁻, thus meeting the requirements of dyes suitable for DSSCs. ESR and electron absorption and emission spectra of radical anion and dianion of 4 appeared under reduction with a potassium mirror in THF were reported and interpreted based of the DFT calculations.

已提出了一种新的合成五环三苯并恶嗪（TPDO）的方法，该方法涉及将6,8-二-（叔丁基）-3H-苯恶嗪-3-酮与邻氨基苯酚缩合，并且在空间上拥挤了一系列2， 4-二-（叔丁基）-苯并[5,6] [1,4]恶嗪基[2,3-b]苯恶嗪（TPDOs）4已经准备好了。这些化合物可很好地溶于非极性和极性溶剂中，在太阳光谱的最强发射部分吸收，显示出强烈的荧光，并在空气条件下具有出色的光稳定性。X射线衍射研究揭示了杂并五苯核TPDO的平面结构以及其中一些分子在晶体中的π-π堆积。使用电化学方法评估并通过DFT B3LYP / 6–311 ++ G（d，p）方法计算的所研究TPDO的前沿MO的能级位于TiO ₂电导区和氧化还原介体限制的能域之外我^- / I ₃ ^-，从而满足适用于DSSC的染料的要求。报道了在THF中用钾镜还原后出现的4的自由基阴离子和二价阴离子的ESR以及电子吸收和发射光谱，并基于DFT计算进行了解释。