Crystalline Carbazole Based Organic Room-Temperature Phosphorescent Materials

doi:10.7536/PC220439

Since the demonstration of organic room temperature phosphorescence (ORTP) from carbazole in 2008, using carbazole unit to construct ORTP materials has become a feasible approach to developing a series of diverse, high-performance, widely applicable and highly representative ORTP material system. This review paper firstly summarizes three strategies for improving phosphorescence performance of ORTP materials, namely H-aggregation, heavy-atom effect and donor-acceptor structure. Then, the recent progress of crystalline carbazole-based ORTP materials is systematically introduced. Based on these three strategies, triplet relaxation is suppressed, spin-orbital coupling is enhanced, singlet-triplet energy gaps are reduced, and intermolecular charge transfer interactions are strengthened. As a result, the triplet excited states are stabilized, and intersystem crossing is accelerated to facilitate phosphorescence, and thereby realizing long-lifetime high-efficiency crystalline carbazole-based ORTP materials. Their applications in the fields of anti-counterfeiting, information security and bioimaging are briefly discussed.

Contents

1 Introduction

2 Mechanism of organic room-temperature phosphorescence (ORTP)

3 Carbazole based ORTP materials

3.1 Crystallization-induced phosphorescence

3.2 H-aggregation induced phosphorescence

3.3 Heavy-atom effect for ORTP

3.4 Donor-acceptor systems for ORTP

3.5 Benz[f]indole isomer doping inducing ORTP

4 Application of carbazole-based ORTP materials

4.1 Bioimaging and photodynamic therapy

4.2 Information safety

5 Conclusion and outlook

Key words: carbazole, organic room-temperature phosphorescence, intersystem crossing, phosphorescence lifetime, phosphorescence quantum yield

Fig. 1 Structural formulas of several representative ORTP materials

Fig. 2 Milestones in developing carbazole-based ORTP materials during recent years. In 2015, Tang Benzhong et al. observed ORTP with a lifetime of 520 ms from crystalline CzBP[35], Copyright 2015, Wiley-VCH Verlag GmbH & Co. KGaA. In the same year, Huang and An et al. constructed the first H-aggregation stabilized ORTP molecule DPhCzT, with a lifetime of 1.07 s and a phosphorescent quantum yield of 1.25%[36], Copyright 2015, Macmillan. In 2017, An et al. constructed ORTP molecule CPhCz that can be excited with visible light through adjusting the interaction between molecules on the xy plane, with a lifetime of 847.17 ms and a phosphorescent quantum yield of 8.30%[37], Copyright 2017, Wiley-VCH Verlag GmbH & Co. KGaA. In the same year, Lu et al realized ORTP molecules with high luminescence efficiency by connecting chromophores Cz and heavy atoms with flexible alkylation chain, in which CC6PhBr has an ORTP lifetime of 0.20 s and a phosphorescent quantum yield of 39.47%[38], Copyright 2017, The Royal Society of Chemistry. In 2020, Yang et al. constructed the twisted D-A molecule ChrPh2Cz and achieved ORTP with a lifetime of 511 ms and a phosphorescent quantum yield of 1.50%[39], Copyright 2020, Elsevier B.V. In the same year, An et al prepared CzBBr combining crystalline, D-A structure and heavy-atom effect to achieve a high phosphorescent quantum yield reaching 37.96%[40], Copyright 2020, Wiley-VCH Verlag GmbH & Co. KGaA. Later, Liu et al proposed that doping carbazole isomer benzo[F]indole can give rise to ORTP from carbazole derivatives, which was demonstrated by the dependence of delayed photoluminescence spectra on CPhCz/CPhBd (15) ratio[41], Copyright 2021, Macmillan

Fig. 3 (a) Fluorescence, delayed fluorescence, phosphorescence and ultralong phosphorescence processes. Exc, Fluo, DF, Phos and Ultralong Phos denote excitation, fluorescence, delayed fluorescence, phosphorescence and ultralong phosphorescence; S0, Sn, Tn and T n * refer to ground, singlet excited, triplet excited and stabilized triplet excited states, respectively. kr,F, knr,F, kr,F and knr,F are radiative and non-radiative transition rate constants of fluorescence and phosphorescence, respectrively[36], Copyright 2015, Macmillan; (b) Molecular orientations within typical J- and H-aggregates. E(k) gives energy dispersion corresponding to the lowest vibronic band in each aggregate. The band curvature at k = 0 is positive or negative in J- or H-aggregates. The red dot indicates the (k = 0) exciton that is optically allowed from the ground state, |G> (black dot). In J-aggregates, neighboring chromophores are oriented in a head-to-tail way, resulting in a negative excitonic coupling and the placement of the optically allowed (k = 0) Frenkel exciton at the bottom of the exciton band. Conversely, in H-aggregates, the nearest neighbor chromophores are oriented in a more side-by-side way, resulting in a positive excitonic coupling and the placement of the k = 0 exciton at the top of the exciton band. The dispersionless (Einstein) phonons of wave vector q derive from the intramolecular vibrations with frequency ω0. Therefore, energy gap between the one- and two-phonon states within the electronic ground state is equal to ?ω0. Arrows indicate emission pathways at T = 0 K, at which emission originates from the lowest-energy exciton. In J-aggregates, 0-0 emission is strongly allowed, leading to superradiance. In contrast, in H-aggregates, rapid intraband relaxation subsequent to absorption populates the lowest-energy k = π exciton, which cannot radiatively couple to |G>, thereby preventing 0-0 emission (assuming no disorder)[57], Copyright 2015, Macmillan; (c) Schematic representation of parallel, oblique, co-planar inclined and non-planar models for H-aggregation[36]; Copyright 2015, Macmillan

Fig. 4 (a) Emission spectra of CzBP、BCzBP and DBCzBP crystals with delay times (td) of 0 and 0.1 ms; (b) Crystal luminescent photographs of CzBP, BCzBP and DBCzBP under ultraviolet ray (UV) irradiation and CzBP without UV irradiation[35], Copyright 2015, Wiley-VCH Verlag GmbH & Co. KGaA

Fig. 5 (a) Emission spectra of 4-MBACz, 3-MBACz and 2-MBACz crystals with delay times (td) of 0 and 0.1 ms; (b) Crystal structure of 2-MBACz and the torsion angles between MBA and Cz moieties[69], Copyright 2018, Wiley-VCH Verlag GmbH & Co. KGaA; (c) Emission spectra of the crystals for 4-BACz, 3-BACz and 2-BACz with delay times (td) of 0 and 0.1 ms; (d) Comparison on ФP values of 18~23[70], Copyright 2018, The Royal Society of Chemistry

Table 1 Photophysical properties of ORTP materials under crystalline state

compound	$λ e x a$ (nm)	$λ e m b$ (nm)	$τ P c$ (ms)	$Φ P d$ (%)	$k r, P e$ (s^-1)	$k n r, P f$ (s^-1)	$k I S C h$ (s^-1)	Δ $E S T i$ (eV)	ref
CzBP(8)	365	—	517.87	1.40	2.70×10^-2	1.90^g	3.98×10⁶	—	35
BCzBP(16)		—	0.11	0.30	27.30	9.06×10^3g	5.66×10⁶	—	35
DBCzBP(17)		—	0.16	7.50	4.69×10²	5.78×10^3g	1.17×10⁸	—	35
4-MBACz(18)	365	552	222.1	2.6	0.12	4.4^g	—	0.84	35
3-MBACz(19)		548	513.9	0.7	1.40×10^-2	1.9^g	—	0.80	35
2-MBACz(20)		557	865.2	0.1	0.91×10^-3	1.2^g	—	0.76	35
4-BACz(21)	365	549/594	558	6.9	—	—	—	0.74	70
3-BACz(22)		546/592	602	3.4	—	—	—	0.67	70
2-BACz(23)		558/599	568	2.6	—	—	—	0.91	70
CzPCl(25)	365	554	224.07	0.33	1.47×10^-2	4.45	2.07×10⁵	—	40
CzPBr(26)		526	299.42	0.21	0.70×10^-2	3.34	1.81×10⁶	—	40
CzBCl(27)		557	777.37	0.57	0.73×10^-2	1.28	3.47×10⁵	—	40
CzBBr(13)		559	220.24	37.96	1.73	2.82	3.80×10⁷	—	40

Table 1 Photophysical properties of ORTP materials under crystalline state

compound	$λ e x a$ (nm)	$λ e m b$ (nm)	$τ P c$ (ms)	$Φ P d$ (%)	$k r, P e$ (s^-1)	$k n r, P f$ (s^-1)	$k I S C h$ (s^-1)	Δ $E S T i$ (eV)	ref
CzBP(8)	365	—	517.87	1.40	2.70×10^-2	1.90^g	3.98×10⁶	—	35
BCzBP(16)		—	0.11	0.30	27.30	9.06×10^3g	5.66×10⁶	—	35
DBCzBP(17)		—	0.16	7.50	4.69×10²	5.78×10^3g	1.17×10⁸	—	35
4-MBACz(18)	365	552	222.1	2.6	0.12	4.4^g	—	0.84	35
3-MBACz(19)		548	513.9	0.7	1.40×10^-2	1.9^g	—	0.80	35
2-MBACz(20)		557	865.2	0.1	0.91×10^-3	1.2^g	—	0.76	35
4-BACz(21)	365	549/594	558	6.9	—	—	—	0.74	70
3-BACz(22)		546/592	602	3.4	—	—	—	0.67	70
2-BACz(23)		558/599	568	2.6	—	—	—	0.91	70
CzPCl(25)	365	554	224.07	0.33	1.47×10^-2	4.45	2.07×10⁵	—	40
CzPBr(26)		526	299.42	0.21	0.70×10^-2	3.34	1.81×10⁶	—	40
CzBCl(27)		557	777.37	0.57	0.73×10^-2	1.28	3.47×10⁵	—	40
CzBBr(13)		559	220.24	37.96	1.73	2.82	3.80×10⁷	—	40

Fig. 6 (a) PL spectra and emissive photographs of four different 2CzBZL crystals (crst-A~D) under 365 nm UV irradiation and at room temperature; (b) Single crystal structures of crst-A~D and intermolecular interactions[71], Copyright 2019, Elsevier B.V.

Fig. 8 Chemical structures of carbazole-based crystallization-induced ORTP materials

Fig. 9 (a) H aggregates in single crystals of DECzT, CzDClT, DCzPhP and DPhCzT; (b) Steady-state photoluminescence (left) and ultralong phosphorescence (right) spectra of DECzT, CzDClT, DCzPhP and DPhCzT. Insets show the corresponding photographs taken before (left) and after (right) excitation; (c) Normalized steady-state photoluminescence spectra and (d) Lifetime decay curves of DPhCzT powder excited at 365 nm in air, argon, and oxygen, respectively; (e) Time dependency of emission intensity for DPhCzT powder at 530 nm. Scan number was 300, with the excitation switching on and off for 2 and 4 s, respectively[36], Copyright 2015, Macmillan

Fig. 10 (a) H-aggregation dimers of PhCz, CPhCz and BPhCz in single crystals; (b) Excitation spectra and photographs of PhCz, CPhCz and BPhCz excited by visible-light LED[37], Copyright 2017, Wiley-VCH Verlag GmbH & Co. KgaA

Table 2 Photophysical properties of carbazole-based ORTP materials featuring H-aggregation

Compound	$λ e x c$ (nm)	$λ e m d$ (nm)	$τ P e$ (ms)	$Φ P f$ (%)	$k I S C g$ (s^-1)	Δ $E S T h$ (eV)	ref
DECzT(28)^a	365	529/574	1281.59/1347.35	0.6	1.1×10⁶	—	36
DPhCzT(9)^a		530/575	1066.00/1052.18	1.25	2.8×10⁶	—	36
CzDClT(29)^a		543/591	470.82/491.21	2.1	1.1×10⁷	—	36
DCzPhP(30)^a		587/644	208.63/207.11	0.08	1.2×10⁵	—	36
PhCz(31)^a	376	530	646.39	0.7	—	—	37
CPhCz(10)^a	410	570	847.17	8.3	—	—	37
BPhCz(32)^a	388	536	667.03	3.4	—	—	37
CzDClT(29)^b	365	549	0.16×10³	1.14	—	—	74
BiCzDT(33)^b		556	0.34×10³	1.45	—	—	74
TCzT(34)^b		548	0.23×10³	2.10	—	—	74
pCNPhCz(35)^a	365	545/594	0.92×10³	1.8	2.3×10⁶	0.21×10^-1	75
mCNPhCz(36)^a		548/599	0.81×10³	3.7	5.3×10⁶	0.73×10^-2	75
oCNPhCz(37)^a		543/593	0.65×10³	2.9	3.9×10⁶	0.45×10^-2	75
DCNPhCz(38)^a		544/593	0.48×10³	8.6	8.3×10⁶	0.03×10^-2	75
mCNPhCz'(36)^a	295	520	0.41×10²	—	—	—	75
AI-Cz(39)^a	365	520	1.9	—	—	0.29	78
AI-N-Cz(40)^a	365	550	775	—	—	0.09	78
CBM(41)^a	365	548	123.2	1.44	1.0×10⁶	0.41	79
CBM-OCH₃(42)^a			929.1	1.54	1.0×10⁶	0.26	79
CBM-CH₃(43)^a			601.5	1.38	0.9×10⁶	0.03	79

Table 2 Photophysical properties of carbazole-based ORTP materials featuring H-aggregation

Compound	$λ e x c$ (nm)	$λ e m d$ (nm)	$τ P e$ (ms)	$Φ P f$ (%)	$k I S C g$ (s^-1)	Δ $E S T h$ (eV)	ref
DECzT(28)^a	365	529/574	1281.59/1347.35	0.6	1.1×10⁶	—	36
DPhCzT(9)^a		530/575	1066.00/1052.18	1.25	2.8×10⁶	—	36
CzDClT(29)^a		543/591	470.82/491.21	2.1	1.1×10⁷	—	36
DCzPhP(30)^a		587/644	208.63/207.11	0.08	1.2×10⁵	—	36
PhCz(31)^a	376	530	646.39	0.7	—	—	37
CPhCz(10)^a	410	570	847.17	8.3	—	—	37
BPhCz(32)^a	388	536	667.03	3.4	—	—	37
CzDClT(29)^b	365	549	0.16×10³	1.14	—	—	74
BiCzDT(33)^b		556	0.34×10³	1.45	—	—	74
TCzT(34)^b		548	0.23×10³	2.10	—	—	74
pCNPhCz(35)^a	365	545/594	0.92×10³	1.8	2.3×10⁶	0.21×10^-1	75
mCNPhCz(36)^a		548/599	0.81×10³	3.7	5.3×10⁶	0.73×10^-2	75
oCNPhCz(37)^a		543/593	0.65×10³	2.9	3.9×10⁶	0.45×10^-2	75
DCNPhCz(38)^a		544/593	0.48×10³	8.6	8.3×10⁶	0.03×10^-2	75
mCNPhCz'(36)^a	295	520	0.41×10²	—	—	—	75
AI-Cz(39)^a	365	520	1.9	—	—	0.29	78
AI-N-Cz(40)^a	365	550	775	—	—	0.09	78
CBM(41)^a	365	548	123.2	1.44	1.0×10⁶	0.41	79
CBM-OCH₃(42)^a			929.1	1.54	1.0×10⁶	0.26	79
CBM-CH₃(43)^a			601.5	1.38	0.9×10⁶	0.03	79

Fig. 13 (a) Luminescence photographs of CBM, CBM-CH3 and CBM-OCH3 crystals under 365 nm and at different time intervals after UV off; (b) H-aggregation dimers and intermolecular interactions of CBM-OCH3 in single crystals[79], Copyright 2021, The Royal Society of Chemistry

Fig. 14 Chemical structural formula of carbazole-based ORTP materials featuring H-aggregation

Fig. 15 (a) Single-crystal structures of 44[81], Copyright 2012, The Royal Society of Chemistry; (b) Emissive photos of CC4Cl (left), CC4Br (middle), and CC4I (right) under 365 nm UV light; (c) Bimolecular packing of CC2Cl, CC4Cl, CC2Br, CC4Br, CC6Br and CC6Br crystals. Red dashed lines denote the weak interactions[83], Copyright 2016, American Chemical Society

Fig. 16 (a) Fluorescence and phosphorescence quantum yields and average phosphorescence lifetimes of CCnBr and CCnPhBr crystals, as well as emissive photos, under 365 nm; (b) Bimolecular packing modes of CC2Br, CC4Br, CC5Br and CC6Br single crystals. The values are the distances for Br/N, and between two adjacent carbazole groups[38], Copyright 2017, The Royal Society of Chemistry

Fig. 17 Molecular structures of carbazole-based ORTP materials constructed by heavy-atom effect

Table 3 Photophysical properties of carbazole-based ORTP materials with heavy-atom effect

compound	$λ e x b$ (nm)	$λ e m c$ (nm)	$Φ F d$ (%)	$τ P e$ (ms)	$Φ P f$ (%)	$k r, P g$ (s^-1)	$k n r, P h$ (s^-1)	ref
CzBP(8)^a	350	570	—	479	0.30	—	—	62
CzBBP(45)^a		549	—	287	5	—	—	62
CzDPS(46)^a		562	—	394	—	—	—	62
CzBDPS(47)^a		558	—	122	6	—	—	62
CC2Cl(48)^a	370	542	—	0.70×10³	0.1	—	—	83
CC4Cl(49)^a		551	—	0.10×10³	< 0.01	—	—	83
CC2Br(50)^a		544/592	—	0.23×10³	1.8	—	—	83
CC4Br(51)^a		555/604	—	0.85×10²	0.8	—	—	83
CC6Br(53)^a		551/604	—	0.41×10³	0.5	—	—	83
CC4I(54)^a		556/604	—	0.32×10²	2.4	—	—	83
CC2Br(50)^a	280	544/591/644	1.10	0.16×10³	1.6	—	—	38
CC4Br(51)^a		555.5/604.5/661	14.30	0.85×10²	11.1	—	—	38
CC5Br(52)^a		544/585/635	38.40	0.02×10³	2.1	—	—	38
CC6Br(53)^a		—	46.50	—	0	—	—	38
CC2PhBr(55)^a		554/602/660	25.20	0.64×10²	8.9	—	—	38
CC4PhBr(56)^a		555/605/660	26.10	0.34×10³	9.5	—	—	38
CC5PhBr(57)^a		555/604	8.38	1.97×10²	2.75	—	—	38
CC6PhBr(11)^a		554/602/659	33.10	0.20×10³	39.47	—	—	38
PDCz(58)^a	—	507	—	—	5.7	0.06	0.99	84
PDFCz(59)^a	—		—	—	3.8	0.04×10^-1	0.10	84
PDCCz(60)^a	—		—	—	1.6	0.01	0.61	84
PDBCz(61)^a	—		—	—	39.1	0.52	0.81	84
PDICz(62)^a	—		—	—	25.8	4.03	11.60	84
DCzMPh(63)^a	356	431	6.58	0.27×10³	0.98	—	—	88
TCzMPh(64)^a	400	430	13.77	0.28×10³	3.43	—	—	88

Table 3 Photophysical properties of carbazole-based ORTP materials with heavy-atom effect

compound	$λ e x b$ (nm)	$λ e m c$ (nm)	$Φ F d$ (%)	$τ P e$ (ms)	$Φ P f$ (%)	$k r, P g$ (s^-1)	$k n r, P h$ (s^-1)	ref
CzBP(8)^a	350	570	—	479	0.30	—	—	62
CzBBP(45)^a		549	—	287	5	—	—	62
CzDPS(46)^a		562	—	394	—	—	—	62
CzBDPS(47)^a		558	—	122	6	—	—	62
CC2Cl(48)^a	370	542	—	0.70×10³	0.1	—	—	83
CC4Cl(49)^a		551	—	0.10×10³	< 0.01	—	—	83
CC2Br(50)^a		544/592	—	0.23×10³	1.8	—	—	83
CC4Br(51)^a		555/604	—	0.85×10²	0.8	—	—	83
CC6Br(53)^a		551/604	—	0.41×10³	0.5	—	—	83
CC4I(54)^a		556/604	—	0.32×10²	2.4	—	—	83
CC2Br(50)^a	280	544/591/644	1.10	0.16×10³	1.6	—	—	38
CC4Br(51)^a		555.5/604.5/661	14.30	0.85×10²	11.1	—	—	38
CC5Br(52)^a		544/585/635	38.40	0.02×10³	2.1	—	—	38
CC6Br(53)^a		—	46.50	—	0	—	—	38
CC2PhBr(55)^a		554/602/660	25.20	0.64×10²	8.9	—	—	38
CC4PhBr(56)^a		555/605/660	26.10	0.34×10³	9.5	—	—	38
CC5PhBr(57)^a		555/604	8.38	1.97×10²	2.75	—	—	38
CC6PhBr(11)^a		554/602/659	33.10	0.20×10³	39.47	—	—	38
PDCz(58)^a	—	507	—	—	5.7	0.06	0.99	84
PDFCz(59)^a	—		—	—	3.8	0.04×10^-1	0.10	84
PDCCz(60)^a	—		—	—	1.6	0.01	0.61	84
PDBCz(61)^a	—		—	—	39.1	0.52	0.81	84
PDICz(62)^a	—		—	—	25.8	4.03	11.60	84
DCzMPh(63)^a	356	431	6.58	0.27×10³	0.98	—	—	88
TCzMPh(64)^a	400	430	13.77	0.28×10³	3.43	—	—	88

Fig. 18 (a) Molecular geometries of ChrPh2Cz、ChrPh3Cz and ChrPh4Cz single crystals; (b) Photographs of ChrPh2Cz, ChrPh3Cz and ChrPh4Cz crystals taken at different time intervals under (first column) and after (succeeding columns) 365 nm irradiation at 300 K in air[39], Copyright 2020, Elsevier B.V.

Fig. 21 Molecular formula of D-A structured carbazole-based ORTP materials

Table 4 Photophysical properties of D-A structured carbazole-based ORTP materials

compound	$λ e x c$ (nm)	$λ e m d$ (nm)	$τ P e$ (ms)	$Φ P f$ (%)	Δ $E S T g$ (eV)	ref
65^a	—	—	—	—	0.297	89
66^a		—	—	—	0.338	89
67^a		—	—	—	0.264	89
68^a		—	—	—	0.245	89
ChrPh2Cz(12)^a	370	479/554/595	474/503/511	1.5	—	39
ChrPh3Cz(69)^a		447/569/613	43/122/135	0.7	—	39
ChrPh4Cz(70)^a		480/574/618	76/126/143	0.2	—	39
CzBP(8)^a	—	—	—	—	0.199	92
BPy3Cz(72)^a	—	—	—	—	0.007	92
p-NN-Br(75)^b	365	547	134	12.8	—	94
m-NN-Br(76)^b	365	543	219	14.0	—	94

Table 4 Photophysical properties of D-A structured carbazole-based ORTP materials

compound	$λ e x c$ (nm)	$λ e m d$ (nm)	$τ P e$ (ms)	$Φ P f$ (%)	Δ $E S T g$ (eV)	ref
65^a	—	—	—	—	0.297	89
66^a		—	—	—	0.338	89
67^a		—	—	—	0.264	89
68^a		—	—	—	0.245	89
ChrPh2Cz(12)^a	370	479/554/595	474/503/511	1.5	—	39
ChrPh3Cz(69)^a		447/569/613	43/122/135	0.7	—	39
ChrPh4Cz(70)^a		480/574/618	76/126/143	0.2	—	39
CzBP(8)^a	—	—	—	—	0.199	92
BPy3Cz(72)^a	—	—	—	—	0.007	92
p-NN-Br(75)^b	365	547	134	12.8	—	94
m-NN-Br(76)^b	365	543	219	14.0	—	94

Fig. 22 Proposed mechanism of ultralong phosphorescence fromBd doped Cz systems. Left: two charge transfer channels between Bd and Cz during photoexcitation. Type I: electrons from the LUMO of Bd are transferred to the LUMO of Cz. Type II: electrons from the HOMO of Bd are transferred to the HOMO of Cz. Middle: charge-separated states are formed through Cz radical anions diffusing to neighbouring Cz molecules, whereas Bd radical cations are trapped by defects. Right: singlets (for example, S1) and triplets (for example, T1) are generated through charge recombination (CR), accompanied by ISC between them. Phos. = phosphorescence[41], Copyright 2021, Macmillan

Table 5 Photophysical properties of ORTP doping systems

compound			$λ e x a$ (nm)	$λ e m b$ (nm)	$τ P c$ (ms)			$k n r, P f$ (s^-1)	$k I S C g$ (s^-1)	ref
TCz-F(77)	Cm		—	—	727	7.4	0.12	1.51	1.01×10⁷	96
TCz-F(77)	Lab		—	515	48.6	0.8	0.12	1.51	1.01×10⁷	96
TCz-H(78)	Cm		—	—	128	4.6	1.93	40.08	8.08×10⁶	96
TCz-H(78)	Lab		—	530	29.9	0.7	1.93	40.08	8.08×10⁶	96
CNCzBr(80)	Lab/Cm	Lab	365	550	1.4	—	—	—	—	98
		5∶1			25.6	—	—	—	—	98
		1∶1			38.6	—	—	—	—	98
		1∶5			78.2	—	—	—	—	98
		Cm			162.2	—	—	—	—	98
CzPyCb(81)	Lab/Cm	Lab	365	550	39.7	—	—	—	—	98
		3∶1			172.4	—	—	—	—	98
		1∶1			162.3	—	—	—	—	98
		1∶3			170.1	—	—	—	—	98
		Cm			219.4	—	—	—	—	98
CzPyAm(82)	Lab/Cm	Lab	365	550	2.3	—	—	—	—	98
		3∶1			14.4	—	—	—	—	98
		1∶1			29.5	—	—	—	—	98
		1∶3			101.1	—	—	—	—	98
		Cm			436.2	—	—	—	—	98
CzPyCN(83)	Lab/Cm	Lab	365	550	2.2	—	—	—	—	98
		3∶1			24.5	—	—	—	—	98
		1∶1			351.2	—	—	—	—	98
		1∶3			506.2	—	—	—	—	98
		Cm			744.4	—	—	—	—	98
CzPyBr(84)	Lab/Cm	Lab	365	550	8.1	—	—	—	—	98
		3∶1			275.3	—	—	—	—	98
		1∶1			357.5	—	—	—	—	98
		1∶3			788.3	—	—	—	—	98
		Cm			1132.8	—	—	—	—	98
WAG(85)			300	544	940	5.5	5.9×10^-2	1.0	5.6×10⁶	99
			320		933	3.5	3.8×10^-2	1.0	3.6×10⁶	99
			340		923	3.1	3.4×10^-2	1.0	3.2×10⁶	99
			365		933	3.4	3.6×10^-2	1.0	3.5×10⁶	99
			380		923	3.3	3.6×10^-2	1.0	3.4×10⁶	99
			400		922	3.3	3.6×10^-2	1.0	3.4×10⁶	99
			420		905	3.4	3.8×10^-2	1.1	3.5×10⁶	99
			440		511	4.1	8.0×10^-2	1.9	4.2×10⁶	99
			460		88	3.3	3.8×10^-2	11.0	3.4×10⁶	99
			480		84	8.1	9.6×10^-2	10.9	8.3×10⁶	99

Table 5 Photophysical properties of ORTP doping systems

compound			$λ e x a$ (nm)	$λ e m b$ (nm)	$τ P c$ (ms)			$k n r, P f$ (s^-1)	$k I S C g$ (s^-1)	ref
TCz-F(77)	Cm		—	—	727	7.4	0.12	1.51	1.01×10⁷	96
TCz-F(77)	Lab		—	515	48.6	0.8	0.12	1.51	1.01×10⁷	96
TCz-H(78)	Cm		—	—	128	4.6	1.93	40.08	8.08×10⁶	96
TCz-H(78)	Lab		—	530	29.9	0.7	1.93	40.08	8.08×10⁶	96
CNCzBr(80)	Lab/Cm	Lab	365	550	1.4	—	—	—	—	98
		5∶1			25.6	—	—	—	—	98
		1∶1			38.6	—	—	—	—	98
		1∶5			78.2	—	—	—	—	98
		Cm			162.2	—	—	—	—	98
CzPyCb(81)	Lab/Cm	Lab	365	550	39.7	—	—	—	—	98
		3∶1			172.4	—	—	—	—	98
		1∶1			162.3	—	—	—	—	98
		1∶3			170.1	—	—	—	—	98
		Cm			219.4	—	—	—	—	98
CzPyAm(82)	Lab/Cm	Lab	365	550	2.3	—	—	—	—	98
		3∶1			14.4	—	—	—	—	98
		1∶1			29.5	—	—	—	—	98
		1∶3			101.1	—	—	—	—	98
		Cm			436.2	—	—	—	—	98
CzPyCN(83)	Lab/Cm	Lab	365	550	2.2	—	—	—	—	98
		3∶1			24.5	—	—	—	—	98
		1∶1			351.2	—	—	—	—	98
		1∶3			506.2	—	—	—	—	98
		Cm			744.4	—	—	—	—	98
CzPyBr(84)	Lab/Cm	Lab	365	550	8.1	—	—	—	—	98
		3∶1			275.3	—	—	—	—	98
		1∶1			357.5	—	—	—	—	98
		1∶3			788.3	—	—	—	—	98
		Cm			1132.8	—	—	—	—	98
WAG(85)			300	544	940	5.5	5.9×10^-2	1.0	5.6×10⁶	99
			320		933	3.5	3.8×10^-2	1.0	3.6×10⁶	99
			340		923	3.1	3.4×10^-2	1.0	3.2×10⁶	99
			365		933	3.4	3.6×10^-2	1.0	3.5×10⁶	99
			380		923	3.3	3.6×10^-2	1.0	3.4×10⁶	99
			400		922	3.3	3.6×10^-2	1.0	3.4×10⁶	99
			420		905	3.4	3.8×10^-2	1.1	3.5×10⁶	99
			440		511	4.1	8.0×10^-2	1.9	4.2×10⁶	99
			460		88	3.3	3.8×10^-2	11.0	3.4×10⁶	99
			480		84	8.1	9.6×10^-2	10.9	8.3×10⁶	99

Fig. 24 Chemical structures of ORTP doping systems

Fig. 25 (a) Top-down and Bottom-up synthetic routes of OSNs-T and OSNs-B, respectively; (b) Ultralong phosphorescence and fluorescence imaging of a mouse with the subcutaneous inclusions of OSNs (1.6 × 10-6 mol·L-1)[108], Copyright 2017, Wiley-VCH Verlag GmbH & Co. KGaA; (c) In vivo phosphorescence imaging based on 4-BACz, 3-BACz, 2-BACz NPs[70], Copyright 2019, The Royal Society of Chemistry; (d) In vivo afterglow imaging of m-PBCM in mouse sentinel lymph nodes[109], Copyright 2017, Wiley-VCH Verlag GmbH & Co. KGaA

Fig.27 Molecular structures of carbazole-based ORTP materials used for biological imaging applications

Fig. 28 Advanced encryption applications based on the differences of ORTP properties. (a) Number “6” pattern marked by m-BrTCz (black) and o-BrTCz (gray) with differentΦP[123], Copyright 2018, Wiley-VCH Verlag GmbH & Co. KGaA; (b) Color-coded and time-resolved applications based on m-BrTCz. White and yellow emissions were from amorphous and crystalline states[62], Copyright 2016, Wiley-VCH Verlag GmbH & Co. KGaA; (c) Illustration of the character “8” arranged by Br-AI-Cz with yellow ORTP, Cl-AI-Cz and F-AI-Cz in the crystalline states[125], Copyright 2020, Chinese Chemical Society & SIOC, CAS; (d) Dual-encryption application based on different ORTP properties of visible-light excitable CPhCz, only UV excitable BPhCz and 9AC without ORTP[37], Copyright 2017, Wiley-VCH Verlag GmbH & Co. KGaA.

Fig. 29 Molecular structures of carbazole-based ORTP materials used for cryptographic applications

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Crystalline Carbazole Based Organic Room-Temperature Phosphorescent Materials

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Crystalline Carbazole Based Organic Room-Temperature Phosphorescent Materials