Abstract: A near infrared dye comprising a counterion and a structure of Formula I wherein the at least one of R1 and R2are 1-(thiophen-2-yl)piperidine, 1-(thieno[3,2-b]thiophen-2-yl)piperidine or 1-([2,2?-bithiophen]-5-yl)piperidine, and X, R, R3-R4, R19, R20 and R22-R29 are disclosed herein. Materials and compositions comprising the NIR dye can absorb light in the NIR I & II regions and then the energy can be released in the form of light (fluorescence) or heat (non-radiative). The dyes can also convert the absorbed light to heat and ultrasound waves via the photoacoustic effect. The photoacoustic effect can be used in photoacoustic tomography to image biological materials or processes. Methods for synthesizing the NIR dyes and materials comprising the same are also disclosed.