PDF
Abstract
Organic room-temperature phosphorescence (RTP) materials have garnered considerable attention in the fields of biosensing, optoelectronic devices, and anticounterfeiting because of their substantial Stokes shifts, tunable emission wavelengths, and prolonged lifetimes. These materials offer remarkable advantages for biological imaging applications by effectively reducing environmental autofluorescence and enhancing imaging resolution. Recently, host–guest systems have been employed as efficient approaches to fabricate pure-organic RTP materials for bioimaging, providing benefits such as controllable preparation and flexible modulation. Consequently, an increasing number of corresponding studies are being reported; however, a comprehensive systematic review is still lacking. Therefore, we summarize recent advances in the development of pure-organic RTP materials using host–guest systems with regard to bioimaging, including rigid matrices and sensitization. The challenge and potential of RTP for biological imaging are also proposed to promote the biomedical applications of organic RTP materials with excellent optical properties.
Keywords
Room-temperature phosphorescence
/
Host–guest system
/
Rigid matrix
/
Biological imaging
Cite this article
Download citation ▾
Zhiqin Wu, Yang Li, Xiang Ma.
Recent Advances in Pure-Organic Host–Guest Room-Temperature Phosphorescence Systems Toward Bioimaging.
Transactions of Tianjin University, 2023, 29(6): 432-443 DOI:10.1007/s12209-023-00375-w
| [1] |
Gu F, Ma XA Stimuli-responsive polymers with room-temperature phosphorescence. Chem A Eur J, 2021, 28(15): e202104131.
|
| [2] |
Song JM, Ma LW, Sun SY, et al. Reversible multilevel stimuli-responsiveness and multicolor room-temperature phosphorescence emission based on a single-component system. Angew Chem Int Ed, 2022, 61(29): e202206157.
|
| [3] |
Lin XH, Xu C, Qiu YY, et al. Emission-tunable room-temperature phosphorescent two-dimensional polymer network via a photo-cross-linking reaction. Ind Eng Chem Res, 2023, 62(33): 13053-13060.
|
| [4] |
Wu Z, Nitsch J, Marder TB Persistent room-temperature phosphorescence from purely organic molecules and multi-component systems. Adv Opt Mater, 2021, 9(20): 2100411.
|
| [5] |
Liu JC, Zhang HY, Wang N, et al. Template-modulated afterglow of carbon dots in zeolites: room-temperature phosphorescence and thermally activated delayed fluorescence. ACS Mater Lett, 2019, 1(1): 58-63.
|
| [6] |
Ji MX, Ma X Recent progress of organic room-temperature phosphorescent materials towards application. Ind Chem Mater, 2023, 1: 582-594.
|
| [7] |
Yang J, Zhen X, Wang B, et al. The influence of the molecular packing on the room temperature phosphorescence of purely organic luminogens. Nat Commun, 2018, 9(1): 840.
|
| [8] |
Zhou YD, Lu S, Zhi JH, et al. Microscopic afterglow bioimaging by ultralong organic phosphorescent nanoparticles in living cells and zebrafish. Anal Chem, 2021, 93(16): 6516-6522.
|
| [9] |
Zhao WJ, Cheung TS, Jiang N, et al. Boosting the efficiency of organic persistent room-temperature phosphorescence by intramolecular triplet-triplet energy transfer. Nat Commun, 2019, 10(1): 1595.
|
| [10] |
Wang X, Shi HF, Ma HL, et al. Organic phosphors with bright triplet excitons for efficient X-ray-excited luminescence. Nat Photonics, 2021, 15(3): 187-192.
|
| [11] |
Gu L, Shi HF, Bian LF, et al. Colour-tunable ultra-long organic phosphorescence of a single-component molecular crystal. Nat Photonics, 2019, 13(6): 406-411.
|
| [12] |
Li H, Li HH, Wang W, et al. Stimuli-responsive circularly polarized organic ultralong room temperature phosphorescence. Angew Chem Int Ed Engl, 2020, 59(12): 4756-4762.
|
| [13] |
Liang YC, Shang Y, Liu KK, et al. Water-induced ultralong room temperature phosphorescence by constructing hydrogen-bonded networks. Nano Res, 2020, 13(3): 875-881.
|
| [14] |
Mellerup SK, Wang SN Boron-based stimuli responsive materials. Chem Soc Rev, 2019, 48(13): 3537-3549.
|
| [15] |
Zhou YS, Qin W, Du C, et al. Long-lived room-temperature phosphorescence for visual and quantitative detection of oxygen. Angew Chem Int Ed, 2019, 58(35): 12102-12106.
|
| [16] |
Xu YZ, Xu RH, Wang Z, et al. Recent advances in luminescent materials for super-resolution imaging via stimulated emission depletion nanoscopy. Chem Soc Rev, 2021, 50(1): 667-690.
|
| [17] |
Jiang YY, Huang JG, Zhen X, et al. A generic approach towards afterglow luminescent nanoparticles for ultrasensitive in vivo imaging. Nat Commun, 2019, 10(1): 2064.
|
| [18] |
Huang QQ, Gao HQ, Yang SM, et al. Ultrastable and colorful afterglow from organic luminophores in amorphous nanocomposites: advanced anti-counterfeiting and in vivo imaging application. Nano Res, 2020, 13(4): 1035-1043.
|
| [19] |
Liao QY, Gao QH, Wang JQ, et al. 9, 9-dimethylxanthene derivatives with room-temperature phosphorescence: substituent effects and emissive properties. Angew Chem Int Ed Engl, 2020, 59(25): 9946-9951.
|
| [20] |
Gao R, Mei X, Yan DP, et al. Nano-photosensitizer based on layered double hydroxide and isophthalic acid for singlet oxygenation and photodynamic therapy. Nat Commun, 2018, 9(1): 2798.
|
| [21] |
Xu YW, Xu P, Hu DH, et al. Recent progress in hot exciton materials for organic light-emitting diodes. Chem Soc Rev, 2021, 50(2): 1030-1069.
|
| [22] |
Zhan G, Liu ZW, Bian ZQ, et al. Recent advances in organic light-emitting diodes based on pure organic room temperature phosphorescence materials. Front Chem, 2019, 7: 305.
|
| [23] |
Sun H, Zhu LL Achieving purely organic room temperature phosphorescence in aqueous solution. Aggregate, 2022, 4(1): e253.
|
| [24] |
Ma LW, Liu YW, Tian H, et al. Switching singlet exciton to triplet for efficient pure organic room-temperature phosphorescence by rational molecular design. JACS Au, 2023, 3(7): 1835-1842.
|
| [25] |
Sasikumar D, John AT, Sunny J, et al. Access to the triplet excited states of organic chromophores. Chem Soc Rev, 2020, 49(17): 6122-6140.
|
| [26] |
Hirata S Ultralong-lived room temperature triplet excitons: molecular persistent room temperature phosphorescence and nonlinear optical characteristics with continuous irradiation. J Mater Chem C, 2018, 6(44): 11785-11794.
|
| [27] |
Yan ZA, Ma XA External heavy-atom activated phosphorescence of organic luminophores in a rigid fluid matrix. ACS Mater Lett, 2022, 4(12): 2555-2561.
|
| [28] |
Bolton O, Lee K, Kim HJ, et al. Activating efficient phosphorescence from purely organic materials by crystal design. Nat Chem, 2011, 3(3): 205-210.
|
| [29] |
Cai SZ, Shi HF, Tian D, et al. Enhancing ultralong organic phosphorescence by effective π-type halogen bonding. Adv Funct Mater, 2018, 28(9): 1705045.
|
| [30] |
Yuan J, Wang YR, Li L, et al. Activating intersystem crossing and aggregation coupling by CN-substitution for efficient organic ultralong room temperature phosphorescence. J Phys Chem C, 2020, 124: 10129-10134.
|
| [31] |
He ZK, Zhao WJ, Lam JWY, et al. White light emission from a single organic molecule with dual phosphorescence at room temperature. Nat Commun, 2017, 8(1): 416.
|
| [32] |
Yuan WZ, Shen XY, Zhao H, et al. Crystallization-induced phosphorescence of pure organic luminogens at room temperature. J Phys Chem C, 2010, 114(13): 6090-6099.
|
| [33] |
Li WL, Huang QY, Mao Z, et al. Selective expression of chromophores in a single molecule: soft organic crystals exhibiting full-colour tunability and dynamic triplet-exciton behaviours. Angew Chem Int Ed, 2019, 59(9): 3739-3745.
|
| [34] |
Yan X, Peng H, Xiang Y, et al. Recent advances on host-guest material systems toward organic room temperature phosphorescence. Small, 2022, 18(1): e2104073.
|
| [35] |
Wang Z, Zhu CY, Wei ZW, et al. Breathing-ignited long persistent luminescence in a resilient metal–organic framework. Chem Mater, 2020, 32(2): 841-848.
|
| [36] |
Gao J, Zhao YY, You XX, et al. Theoretical search of a simple characteristic for long-lived organic room-temperature phosphorescence materials with H aggregation. J Mater Chem C, 2022, 10(14): 5425-5432.
|
| [37] |
Shi HF, Yao W, Ye WP, et al. Ultralong organic phosphorescence: from material design to applications. Acc Chem Res, 2022, 55(23): 3445-3459.
|
| [38] |
Ma XA, Wang JE, Tian H Assembling-induced emission: an efficient approach for amorphous metal-free organic emitting materials with room-temperature phosphorescence. Acc Chem Res, 2019, 52(3): 738-748.
|
| [39] |
Qu DH, Wang QC, Zhang QW, et al. Photoresponsive host–guest functional systems. Chem Rev, 2015, 115(15): 7543-7588.
|
| [40] |
Pedersen CJ Cyclic polyethers and their complexes with metal salts. J Am Chem Soc, 1967, 89(26): 7017-7036.
|
| [41] |
Zhang QW, Yao XY, Qu DH, et al. Multistate self-assembled micro-morphology transitions controlled by host–guest interactions. Chem Commun, 2014, 50(13): 1567-1569.
|
| [42] |
Ma XA, Tian H Stimuli-responsive supramolecular polymers in aqueous solution. Acc Chem Res, 2014, 47(7): 1971-1981.
|
| [43] |
Wankar J, Kotla NG, Gera S, et al. Recent advances in host–guest self-assembled cyclodextrin carriers: implications for responsive drug delivery and biomedical engineering. Adv Funct Mater, 2020, 30(44): 1909049.
|
| [44] |
Crini G, Fourmentin S, Fenyvesi É, et al. Cyclodextrins, from molecules to applications. Environ Chem Lett, 2018, 16(4): 1361-1375.
|
| [45] |
Li D, Liu ZJ, Fang MM, et al. Ultralong room-temperature phosphorescence with second-level lifetime in water based on cyclodextrin supramolecular assembly. ACS Nano, 2023, 17(13): 12895-12902.
|
| [46] |
Turro NJ, Bolt JD, Kuroda Y, et al. A study of the kinetics of inclusion of halonaphthalenes with β-cyclodextrin via time correlated phosphorescence. Photochem Photobiol, 1982, 35(1): 69-72.
|
| [47] |
Li DF, Lu FF, Wang JE, et al. Amorphous metal-free room-temperature phosphorescent small molecules with multicolor photoluminescence via a host–guest and dual-emission strategy. J Am Chem Soc, 2018, 140(5): 1916-1923.
|
| [48] |
Hayduk M, Schaller T, Niemeyer FC, et al. Phosphorescence induction by host-guest complexation with cyclodextrins–the role of regioisomerism and affinity. Chem A Eur J, 2022, 28(51): e202201081.
|
| [49] |
Gong YF, Chen H, Ma XA, et al. A cucurbit[7]uril based molecular shuttle encoded by visible room-temperature phosphorescence. ChemPhysChem, 2015, 17(12): 1934-1938.
|
| [50] |
Wang J, Huang ZZ, Ma X, et al. Visible-light-excited room-temperature phosphorescence in water by cucurbit[8]uril-mediated supramolecular assembly. Angew Chem Int Ed Engl, 2020, 59(25): 9928-9933.
|
| [51] |
Chen YH, Yang JS, Zhang S, et al. Construction of a room-temperature phosphorescence system by cucurbit[8]uril-based supramolecular assembly. J Incl Phenom Macrocycl Chem, 2022, 102(5): 429-437.
|
| [52] |
Xu TY, Liu FB, Hu XC, et al. Cucurbit[n]uril-based host-guest interaction enhancing organic room-temperature phosphorescence of phthalic anhydride derivatives in aqueous solution. New J Chem, 2022, 46(23): 11025-11029.
|
| [53] |
Ma XK, Zhou XL, Wu J, et al. Two-photon excited near-infrared phosphorescence based on secondary supramolecular confinement. Adv Sci, 2022, 9(18): e2201182.
|
| [54] |
Wang CH, Liu YH, Liu Y Near-infrared phosphorescent switch of diarylethene phenylpyridinium derivative and cucurbit[8]uril for cell imaging. Small, 2022, 18(21): e2201821.
|
| [55] |
Wang YS, Gao HQ, Yang JE, et al. High performance of simple organic phosphorescence host–guest materials and their application in time-resolved bioimaging. Adv Mater, 2021, 33(18): 2007811.
|
| [56] |
Chang K, Xiao LY, Fan YY, et al. Lighting up metastasis process before formation of secondary tumor by phosphorescence imaging. Sci Adv, 2023, 9(20): eadf6757.
|
| [57] |
Dai WB, Zhang YH, Wu XH, et al. Red-emissive organic room-temperature phosphorescence material for time-resolved luminescence bioimaging. CCS Chem, 2022, 4(8): 2550-2559.
|
| [58] |
Si YY, Zhao YY, Dai WB, et al. Organic host-guest materials with bright red room-temperature phosphorescence for persistent bioimaging. Chin J Chem, 2023, 41(13): 1575-1582.
|
| [59] |
Xiao FM, Gao HQ, Lei YX, et al. Guest-host doped strategy for constructing ultralong-lifetime near-infrared organic phosphorescence materials for bioimaging. Nat Commun, 2022, 13(1): 186.
|
| [60] |
Ding BB, Ma XA, Tian H Recent advances of pure organic room temperature phosphorescence based on functional polymers. Acc Mater Res, 2023, 4(10): 827-838.
|
| [61] |
Cai SZ, Shi HF, Li JW, et al. Visible-light-excited ultralong organic phosphorescence by manipulating intermolecular interactions. Adv Mater, 2017, 29(35): 1701244.
|
| [62] |
Shi HF, Zou LA, Huang KW, et al. A highly efficient red metal-free organic phosphor for time-resolved luminescence imaging and photodynamic therapy. ACS Appl Mater Interfaces, 2019, 11(20): 18103-18110.
|
| [63] |
Wang X, Sun WJ, Shi HF, et al. Organic phosphorescent nanoscintillator for low-dose X-ray-induced photodynamic therapy. Nat Commun, 2022, 13(1): 5091.
|
| [64] |
Dang QX, Jiang YY, Wang JF, et al. Room-temperature phosphorescence resonance energy transfer for construction of near-infrared afterglow imaging agents. Adv Mater, 2020, 32(52): 2006752.
|
| [65] |
Xing WW, Wang HJ, Liu ZX, et al. Photoreaction boosting phosphorescence cascade energy transfer based on cucurbit[8]uril biaxial polypseudorotaxane. Adv Opt Mater, 2023, 11(7): 2202588.
|
| [66] |
Dai XY, Huo M, Dong XY, et al. Noncovalent polymerization-activated ultrastrong near-infrared room-temperature phosphorescence energy transfer assembly in aqueous solution. Adv Mater, 2022, 34(38): e2203534.
|