Novel benzofuran-/benzothiophene-incorporated triphyrins(2.1.1) were synthesized using readily available precursors under mild reaction conditions. The X-ray structure revealed that the benzofuran-incorporated triphyrin(2.1.1) macrocycle was slightly ruffled. The triphyrins(2.1.1) exhibit more absorption in the NIR region compared to previously reported dibenzofuran-/dibenzothiophene-incorporated hybrid macrocycles. The benzofuran-incorporated triphyrin shows significant red shift in absorption bands compared to that of benzothiophene-based triphyrin due to its more coplanar arrangement as supported by X-ray and DFT studies.