Synthetic manipulation of the torsion angles in non-planar pi-conjugated dibenzo[g,p]chrysene (DBC) core was described. We prepared DBC scaffolds having four bromines at two bays, and found lithium -bromine exchange procedures enabled to create new DBC derivatives. Crystallographic analyses revealed the largest torsion angle of 57.4 degrees in a tetra-sulfonyl-substituted DBC and the smallest torsion angle 31.8 degrees in a bis-silicon-bridged DBC. With the aid of computational method, these results mean the skeletal fused ring is flexibly movable within a range of 25.6 degrees. This study provides us an intellectual basis for development of distortion-featured functional organic materials. (c) 2022 Elsevier Ltd. All rights reserved.
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