Polycyclic aromatic hydrocarbon compounds (PAHs) have great applications on optoelectronic devices such as OFET, OLED, solar cells, sensors and liquid-crystal displays. Introduction of the alkynylated groups to PAHs, improve the thermal stability as well as the electron mobility which helps in fabrication of optoelectronic devices. Molecules such as 2,6,9,10-tetraalkynylatedanthracene show great application on OFETs devices. Band-gap and electronic mobility, get greatly influence by functionalizing the alkynylated units present in 2,6,9,10-tetraalkynylatedanthracene. So far the synthesis of unsymmetrical 2,6,9,10-tetraalkynylatedanthracene compounds is possible by multi-step reactions only as reported in literature. For the first time, we report a one-pot single-step synthesis of nine new symmetric highly p-conjugated 2,6,9,10-tetraalkynylatedanthracenes, starting from 2,6,9,10-tetrabromoanthracenes employing Pd(CH3CN)2Cl2 /cataCXium®A as catalyst. Out of nine compounds, five were characterized by SCXRD, two of these exhibited various interactions in solid state like π-π, symmetrical bifurcated Cphenyl-H.....π (C≡C) and T-shaped Cphenyl-H.....π (C≡C) which improve the stability and rigidity by shortening the intermolecular distance. All compounds are highly emissive in low to moderately polar solvents (φ = 30-69%, in CHCl3), thin-film as well as powder state and behave as semiconductors with low to moderate band gap (1.79-2.04 eV) which are suitable material for optoelectronic devices. D-π-A-π-D motif containing two compounds show positive solvatochromism as well as halochromism.

Tunable photophysical properties of tetraethynylated anthracenes synthesized via multi-fold Sonogashira coupling

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