A new enantiomerically pure compound was synthesized by the single step reduced reaction from 2-(imidazo[1,2-a]pyridin-2-yl)-2-oxo-N-(pyridin-2-yl)acetamide via chiral induction with D-tartaric acid in good yield. Single crystal data confirm this compound crystallizes in chiral space group P2 1 . Transmission spectrum reveals that the crystal has low UV cut-off of 372 nm and has a good transmittance in the entire visible and near-infrared (NIR)region to 1100 nm, indicating its optical application. Kurtz powder test shows a good second harmonic generation (SHG) which also demonstrates its chiral structure. Moreover, this material exhibits blue phosphorescence with quantum yield of 3.6% and unusually NIR absorption between 1500 nm and 2500 nm. Therefore, this new chiral crystal is a promising multifunctional material for the blue phosphorescence, NIR absorption and nonlinear optical (NLO) applications.Organic noncentrosymmetric materials which probably have nonlinear optical (NLO) properties have received considerable attention due to their potential applications in frequency conversion, optical limiting, electro-optic modulation and in the investigation of nonlocal effects. Such materials offer numerous design possibilities and larger and faster optical nonlinearities when compared to their inorganic counterparts. 1,2 The strong macroscopic second-order nonlinearity requires a noncentrosymmetric crystal structure. Unfortunately, only a few molecules crystallize in noncentrosymmetric style, and even fewer of them are useful for NLO materials. Many approaches have been developed to produce noncentrosymmetric structure, e.g. designing molecules with small ground-state dipole moments, 3 choosing pure enantiomers, 4-7 halogen hydrogen bonding, 8,9 meta-substitution 10 and so on. These strategies have generated many noncentrosymmetric and/or chiral organic crystals. [11][12][13][14][15] On the other hand, dyes with strong absorption in the near-infrared (NIR) region of electromagnetic radiation (approximately 750-3000 nm) are presently finding widespread applications in diverse fields such as the conversion of solar energy to electrical energy, optical communications, bioimaging, biosensors, thermal therapy and optoelectronics. 16-21 NIR organic materials can potentially be used in NIR devices, due to their low cost, light weight and flexibility. However, commercially available NIR organic materials with absorption in the range of 1000-2000 nm are extremely rare. 20,22 Moreover, many organic compounds with conjugated bond systems are known to be deeply colored and act as NIR absorbers. [23][24][25][26][27] To date, purely organic luminogenic molecules that are also phosphorescent are very rare, 28 because the highly bonded nature of electrons in metal-free organic molecules makes them little freedom and less impetus to emit from triplet states. Phosphorescence is therefore generally regarded as a solely inorganic or organometallic property. Although most purely organic materials have been considered to be nonphosphoresc...