The fabrication of a high-performance, low voltage operated flexible organic photodetector (OPD) based on solution self-assembled crystalline thin film of a small molecule, viz, 6,13 bis(tri-isopropylsilylethynyl) pentacene (Tips pentacene) is reported. The OPD demonstrated excellent photodetection ability under range of visible light as well as under UV light, with low illumination intensity. Under 590 nm illumination (5.6 µW/cm2), the device showcased photo to dark current ratio (Iphoto/Idark), ca. 25, photoresponsivity (P) of 89 mA/W, detectivity of 1.81×1010 jones at 1 V bias and response times of 0.04/0.2 sec. Photocurrent modulation of the OPD has been realized by varying the channel width, incident wavelength, applied bias and the illumination intensity. The OPD exhibited excellent photodetection ability under different tensile bending, with roughly 55 % decline in Iphoto/Idark value and 30 % decline in R value under bending radius of 7.5 mm. The OPD could withstand thousands of repeated bending/folding cycles, and regain its initial photoresponse characteristics, if put at rest for 2 hours. The excellent device performances with its precise tuning via various input stimuli suggests that present OPD have great potential for future low cost, low energy and wearable optoelectronics.