Structural Expansion of Dibenzo[b,d]thiophene Sulfone through Functionalization at Bay Positions

Area of Science:

• Organic Chemistry
• Materials Science

Background:

• Dibenzothiophene sulfones are important scaffolds in organic electronics.
• Understanding structure-property relationships is crucial for designing new materials.

Purpose of the Study:

• To synthesize novel 1,9-disubstituted dibenzothiophene sulfone derivatives.
• To investigate the influence of steric factors on synthetic outcomes.
• To explore annulation reactions for extended π-conjugated systems.

Main Methods:

• Synthesis of 1,9-dibromodibenzo[b,d]thiophene sulfone.
• Generation and trapping of dilithio intermediates with various electrophiles.
• Annulation reactions to form extended π-conjugated systems.
• Characterization using cyclic voltammetry, UV-vis spectroscopy, and DFT calculations.

Main Results:

• Successfully synthesized 1-substituted and 1,9-disubstituted dibenzothiophene sulfone derivatives.
• Demonstrated the effect of steric hindrance on regioselectivity during electrophilic trapping.
• Obtained extended π-conjugated systems through annulation reactions.
• Characterized the electronic and optical properties of the synthesized compounds.

Conclusions:

• Steric factors play a significant role in controlling the substitution patterns of dibenzothiophene sulfone derivatives.
• The developed synthetic routes provide access to diverse functionalized molecules.
• The characterized compounds show potential for applications in organic electronics and materials science.