We report a soluble pentacene derivative, 6,13-bis(2-(trimethylsilyl)ethynyl) pentacene, can be used for efficient extraction of metallic single-walled carbon nanotubes (SWCNTs), which is proven by resonance Raman spectroscopy (RRS), Vis-NIR absorption spectroscopy and conductivity measurements. RRS studies reveal that the separation is solvent-dependent and is more efficient for small diameter tubes. Theoretical simulation suggests that the adsorption of pentacene on (7,7) metallic SWCNT is about 34% more favorable than that on (13,0) semiconducting SWCNT. This work provides a new direction in seeking reagents to facilitate high efficiency and nondestructive separation of metallic and semiconducting SWCNTs. (C) 2009 Elsevier B. V. All rights reserved.