Journal
CHEMPLUSCHEM
Volume 86, Issue 1, Pages 130-136Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.202000800
Keywords
charge transport; luminescence; organic materials; phospholes; thiophenes
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This study investigated the impact of heterole-fused structures on the physicochemical properties of thiophene-fused naphthodiphospholes. Isomers with different fused structures exhibited distinct phosphorescence or fluorescence characteristics, as well as varied stacking arrangements. The controlled fusion of heterole rings is revealed as a universal approach to uncover the intrinsic properties of organic functional materials for versatile applications.
For polycyclic aromatics with heterole-fused structures, the orientation of fused heterole rings as well as the geometry of their fused structures has a large impact on the physicochemical properties. In this study, a series of isomers of thiophene-fused naphthodiphospholes was designed and synthesized. Systematic investigation unveiled the explicit impact of heterole-fused structures on their structural and electronic properties. The isomers with 1,2/5,6-fused structure display phosphorescence due to enhanced spin-orbit coupling, whereas the isomers with 2,3/6,7-fused structure exhibit intense fluorescence. The trans isomers exhibited 1D slip pi-stacked arrangement. In contrast, the cis isomers displayed 2D herringbone structure or columnar structure with a cavity. Therefore, the precisely controlled fusion of heterole rings is a universal approach to uncover their intrinsic properties for versatile applications as organic functional materials.
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