Synthesis, Optical Properties, and Crystal Structures
of Dithienostannoles
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Abstract
Reactions of dichlorodiphenylstannane
with 3,3′-dilithio-5,5′-bis(trimethylsilyl)-2,2′-bithiophene
and 3,3′-dilithio-2,2′-di(benzo[<i>b</i>]thiophene)
gave 1,1-diphenyl-3,6-bis(trimethylsilyl)dithienostannole (<b>DTSn1</b>) and di(benzo[<i>b</i>]thieno)-1,1-diphenylstannole (<b>DTSn2</b>), respectively. Optical properties of the dithienostannoles
and the results of DFT calculations on a model suggested an in-phase
interaction between Sn σ* and bithiophene π* orbitals,
stabilizing the LUMO. Interestingly, <b>DTSn1</b> showed crystallization-enhanced
emission and the photoluminescence (PL) quantum yield of the crystals
was determined to be higher by about 20 times than that in the amorphous
and solution phase, while <b>DTSn2</b> exhibited moderate PL
efficiency both as crystals and in solution. Crystal structures of
the dithienostannoles were determined by X-ray diffraction studies,
which showed the differences in the molecular packing between <b>DTSn1</b> and <b>DTSn2</b>, being responsible for their
different PL properties in the crystal state