Substituted thiophene-2-carbaldehydes 1a-d were utilized in the synthesis of symmetrically substituted thiazolo [5,4-d]thiazoles 3a-d. Bis(5,thiazoles with thiophene core at the termini are the most employed in the chemistry of materials but exhibit insufficient solubility in majority of organic solvents with notable impact on the low yields of products. Accordingly, the synthetic approach towards 2,5-dithiophen-2-yl-thiazolo [5,4-d]thiazole (3a) and its substituted derivatives 3b-d is discussed under the various reaction conditions. Appropriate structural characterisations are included with emphasis on relationship between structure and physicochemical properties highlighting the UV-Vis and fluorescence.