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RESEARCH PAPER · Chemistry of Materials · 2022

Driving Nonlinear Optical Activity with Dipolar 2-Aminopyrimidinium Cations in (C4H6N3)+(H2PO3)−

Zi‐Peng Zhang, Xin Liu, Xiaomeng Liu, Zhong-Wei Lu, Xin Sui, Bo-Yu Zhen, Zheshuai Lin, Ling Chen, Li‐Ming Wu

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Driving Nonlinear Optical Activity with Dipolar 2-Aminopyrimidinium Cations in (C4H6N3)+(H2PO3)−OriginalA novel 2-(aminomethyl)pyridineH 2 PO 4 crystal with second-order nonlinear optical performance8Cooperative Enhancement of Second Harmonic Generation in an Organic–Inorganic Hybrid Antimony Halide63New Low-Dimensional Lead-Free Perovskite (2-AMP)2BiX7·H2O (X = Cl, Br) Crystals: Synthesis, Stability, and Nonlinear Optical Properties27BaSb(H2PO2)3Cl2: An excellent UV nonlinear optical hypophosphite exhibiting strong second-harmonic generation response32SbHPO3F: 2D van der Waals Layered Phosphite Exhibiting Large Birefringence32Finding a Deep‐UV Borate BaZnB4O8 with Edge‐sharing [BO4] Tetrahedra and Strong Optical Anisotropy20A High‐Performance Nonlinear Optical Crystal with a Building Block Containing Expanded π‐Delocalization95A High‐Performance Nonlinear Optical Crystal with a Building Block Containing Expanded π‐Delocalization5Phosphites: A Nonlinear Optical Materials System with a Wide Band Gap and Moderate Second-Harmonic Generation Effect27K 3 C 6 N 7 O 3 ·2H 2 O: A Multifunctional Nonlinear Optical Cyamelurate Crystal with Colossal π-Conjugated Orbitals44Homochiral Metallohelicates Based on Zinc(II) and Cadmium(II) Clusters with Excellent Thermostability and Remarkable Second-Harmonic Generation12Characteristics of structure, thermal stability and optical properties for a novel NLO crystal (C5H12NO)H2PO48(C 5 H 6.16 N 2 Cl 0.84 )(IO 2 Cl 2 ): a birefringent crystal featuring unprecedented (IO 2 Cl 2 ) − anions and π-conjugated organic cations56A UV solar-blind nonlinear optical crystal with confined π-conjugated groups13C 10 H 10 ClNO 3 : exploration of birefringent crystals in an isoquinoline system20Compounds consisting of coplanar π-conjugated B3O6-typed structures: An emerging source of ultraviolet nonlinear optical materials20Solvent-free synthesis of magnesium phosphite-oxalates that show second-harmonic generation responses5β-(C 3 H 7 N 6 ) 2 Cl 2 ·H 2 O and (C 3 H 7 N 6 )F·H 2 O: two UV birefringent crystals induced by uniformly aligned structural groups35Pb2Cl2(HPO3)(H2O) and Pb3Br2(HPO3)2: Two Phosphite Halides with 3D Structural Networks and Enlarged Birefringence18Atomic Structural Origin of Fictive Temperature Revealed by AZnP3O9 (A=K, Rb) Glasses3Atomic Structural Origin of Fictive Temperature Revealed by AZnP3O9 (A=K, Rb) Glasses2Exploring the thermo-stability and optical characteristics of (Morpholine)2SbCl5 crystal with a non-centrosymmetric structure6Naphthalene-Like Unit That Induces Strong Optical Anisotropy in C10H8NO2Br and C10H8NO2Br·H2O12Design of the Ionic Organic Nonlinear Optical Material NH 4 [LiC 3 H(CH 3 )O 4 ] with Ultrawide Band Gap and Moderate Birefringence79Design of the Ionic Organic Nonlinear Optical Material NH 4 [LiC 3 H(CH 3 )O 4 ] with Ultrawide Band Gap and Moderate Birefringence9From Centrosymmetry to Noncentrosymmetry: Precise Structural Regulation and Characterization on ZnHPO3·2H2O Polymorphs13Beyond π–π Stacking: Understanding Inversion Symmetry Breaking in Crystalline Racemates26C14H10BrNO2: A Birefringent Crystal with an Expanded π-Conjugated Group13α- and β-(C4H5N2O)(IO3)·HIO3: Two SHG Materials Based on Organic–Inorganic Hybrid Iodates14Bulk‐Size and Highly Transparent Composite Phosphor for NIR Spectroscopy8Rational Design of Noncentrosymmetric Organic–Inorganic Hybrids with a π-Conjugated Pyridium-Type Cation for High Nonlinear-Optical Performance19(C 3 N 6 H 7 )BF 4 ·H 2 O and (C 3 N 6 H 7 )SO 3 CH 3 ·H 2 O with large birefringence induced by coplanar π-conjugated [C 3 N 6 H 7 ] + groups33[(C 5 H 6 N 2 ) 2 H](Sb 4 F 13 ): a polyfluoroantimonite with a strong second harmonic generation effect60Crystal clear: unveiling giant birefringence in organic–inorganic cocrystals33Designing promising ultraviolet (UV) birefringent crystals with different hydrogen-bonded phosphate frameworks18Large optical anisotropy in noncentrosymmetric phosphate with pseudo 2D intercalated layer16Recent advances in rational structure design for nonlinear optical crystals: leveraging advantageous templates153Research progress in optical materials with cationic organic planar π-conjugated groups containing CN bonds34Synthesis and Characterization of Metal Iso-cyamelurate K0.5In0.5(H2C6N7O3)2·9H2O with Large Birefringence8Designing Optical Anisotropy: Silver-Aminoalkylpyridine Nitrate Complexes with Tunable Structures3Rational Combination of π‐Conjugated and Non‐π‐Conjugated Groups Achieving Strong Nonlinear Optical Response, Large Optical Anisotropy, and UV Light‐Switchable Fluorescence65(C8H6BrN2O)NO3: A Hybrid Nonlinear Optical Crystal With an Appropriate Birefringence12Centric Sc(HPO3)(H2PO3)(H2O) and Acentric Sc(H2PO3)3: Two Ultraviolet Scandium Phosphite Optical Crystals12A Noncentrosymmetric Metal‐Free Borophosphate: Achieving a Large Birefringence and Excellent Stability by Covalent‐Linkage27Tunable Optical Anisotropy in Rare‐Earth Borates with Flexible [BO3] Clusters7C9H7NBrX (X = Cl, Br, NO3): Three Excellent Birefringent Crystals with Distinct Optical Anisotropy Regulated by Anions34Zn(C6H4NO2)2·4H2O: A Solar-Blind Birefringent Crystal5Intramolecular Hydrogen Bonds Enhance Structure Coplanarity, Resulting in Significant Birefringence in Bridged-Bipyridine Halides7Enhanced UV Nonlinear Optical Properties in Layered Germanous Phosphites through Functional Group Sequential Construction11Enhanced UV Nonlinear Optical Properties in Layered Germanous Phosphites through Functional Group Sequential Construction116[B3O3F4(OH)]2–: A Versatile Hydroxyfluorooxoborate Heteroanion Producing Compounds with Highly Tunable Optical Anisotropy19Noncentrosymmetric Crystal [C10H8NO2]2SiF6·H2O with Large Birefringence12C6N7(NH2)3·H3PO4: Strong Second Harmonic Generation and Giant Birefringence Benefiting from Amino Substitution Strategy24Investigations of structure, thermal stability and optical properties of a new NLO crystal (C3H5N2)+(CF3COO)-0[C8H6BrN2O]Cl and [C8H6IN2O]Cl: Two birefringent crystals with π-conjugated quinazoline groups24-Nitro-phenylalanine Bromides: D−π–A Structural Features and Their Nonlinear and Linear Optical Properties2The synthesis, structures and characterizations of (C5H12NO)4Cd3Cl10·2H2O and (C5H12NO)2BiCl6·H5O2 crystals0Chiral Metal Self‐Assemblies of Zirconium‐Tetrahedra and Their Second Harmonic Generation Activity6Chiral Metal Self‐Assemblies of Zirconium‐Tetrahedra and Their Second Harmonic Generation Activity0Unveiling Noncentrosymmetric Pyridine Carboxylates from Centrosymmetric Templates through Motif Configuration Modulation in Zero-Dimensional System7Unconventional Heterobidentate Coordination of 4‐Hydroxypyridine Leading to Remarkably Strong Second‐Harmonic Generation in Zn(C 5 H 4 NO) 267Unconventional Heterobidentate Coordination of 4‐Hydroxypyridine Leading to Remarkably Strong Second‐Harmonic Generation in Zn(C 5 H 4 NO) 221Unveiling Charge Dependent Law to Enhance Birefringence in 2‐Aminopyrimidine Family21(C 6 H 5 N 2 )HgCl 3 : Discovery of a Polar Hg‐Based Hybrid Halide as Preeminent Nonlinear Optical and Birefringent Material Activated by π‐Conjugated Organic Cation Substitution38(C 5 N 2 H 7 )IO 2 F 2 and (C 3 N 6 H 8 )(IO 2 F 2 ) 2 : two new organic–inorganic hybrid fluoroiodate birefringent crystals7(C 7 H 3 NO 4 ) 2 Sb 2 F 2 ·2H 2 O: a pyridine-based compound shows large optical anisotropy4Bazn2(Hpo3)3: A New Barium Zincophosphite with Short Ultraviolet Cutoff Edge0Exploring ultra-high optical anisotropy in polyiodides7Greatly enhancing birefringence of fluorosilicates through the synergetic effect of functional units13Significant enhancement in the birefringence of metal phosphite halides via the introduction of π-conjugated cations17Synergistic engineering of ultraviolet metal-free crystals with exceptional birefringence via pyridine-derived dimers14[C 2 N 4 H 7 O][NH 2 SO 3 ]: High‐Performance Ultraviolet Nonlinear Optical Crystal with Ditrigon Coupled Guanylurea Group9[C 2 N 4 H 7 O][NH 2 SO 3 ]: High‐Performance Ultraviolet Nonlinear Optical Crystal with Ditrigon Coupled Guanylurea Group48Chiral-Unit-Oriented Design of Non-π-Conjugated Noncentrosymmetric Phosphates with Short Absorption Edges4(C6H10N2)ZnX4·H2O (X=Cl and Br): Excellent nonlinear optical properties and temperature induced photoluminescence for encryption23Engineering an Excellent β ‐BaB 2 O 4 ‐Inspired UV Nonlinear Optical Material Through Secondary Building Unit Substitution21Engineering an Excellent β ‐BaB 2 O 4 ‐Inspired UV Nonlinear Optical Material Through Secondary Building Unit Substitution6(3‐C6H10N2)ZnX4 (X = Cl and Br): Two Excellent UV Nonlinear Optical Crystals Designed by Combination of π‐conjugated and [ZnX4]2− Tetrahedral Units26Rational design of a high-efficiency lead halide organic-inorganic hybrid nonlinear optical switch via molecular engineering5Metal Cation Engineered UV Birefringent Crystals in π‐Conjugated Sulfonates with Record‐High Optical Anisotropy17Extended study of crystal structures, optical properties and vibrational spectra of polar 2-aminopyrimidinium hydrogen phosphite and three centrosymmetric salts - bis(2-aminopyrimidinium) sulfate monohydrate and two 2-aminopyrimidinium hydrogen sulfate polymorphs1Unearthing Hydrogen Bonded Metal‐Free Crystal with Remarkable Optical Anisotropy9Multifunctional Cd‐based Hybrid with Large Birefringence Achieving Excellent Second Harmonic Generation and Reversible Temperature‐Activated Fluorescence for Anti‐counterfeiting16Decoupling the SHG‐Birefringence Trade‐off in UV NLO Materials via Triple‐Control Coordination Engineering: Achieving Synergistic Performance Optimization88Decoupling the SHG‐Birefringence Trade‐off in UV NLO Materials via Triple‐Control Coordination Engineering: Achieving Synergistic Performance Optimization13[CON3H6BF4]: An Efficient Metal‐Free Borate with Optimized Birefringence Achieved by Structural Design Strategy15Giant Birefringence and Solar‐Blind Ultraviolet Transmission by Coordination‐Induced Assembly of π‐Conjugated Pyridine–Carboxylate8Giant Birefringence and Solar‐Blind Ultraviolet Transmission by Coordination‐Induced Assembly of π‐Conjugated Pyridine–Carboxylate24Designing an all-organic wide bandgap ultraviolet nonlinear optical crystal3Unlocking the potential of Indolo-Carbazole Derivatives: first-principles insights into charge injection and optical switching applications7Four Benzoguanamine-Based Birefringent Crystals with Excellent Optical Anisotropy5Designing hybrid zinc-based ultraviolet nonlinear optical crystal with strong NLO response and dual-color luminescence via the integration of two different SHG-active genes6Anion-Ordered [B3O5(OH)2] Induced by Crystal Water with Deep Ultraviolet Transparency and Large Birefringence in Boron-Rich Borophosphates4BaZn2(HPO3)3: A New Barium Zincophosphite with Short Ultraviolet Cutoff Edge2Giant Birefringence Induced by Intermolecular Aromatic Interactions in Hydrogen‐Bonded Organic Frameworks37Pioneering sulfophosphite crystals: Co-assembly of phosphite and sulfate units in novel inorganic architectures0Enhancing Birefringence via a Planar‐Conformation‐Locking Strategy3Anionic Group Trimming Strategy: Oriented Fabrication of Sulfonate UV Birefringent Crystals with High Optical Anisotropy5Quinquevalent phosphorus acids0Effect of Multiple Hydrogen Bonding on the π-Conjugated Groups and Optical Properties in Molecular Crystals5Single Crystal X-Ray Structure Determination and Vibrational Spectroscopy of 2-Aminopyrimidinium Hydrogen Trioxofluorophosphate and bis(2-Aminopyrimidinium) Trioxofluorophosphate0Achieving Ultra‐High Optical Anisotropy via Structural Regulation and Coplanar Engineering of Extended π‐Conjugated [H 2–x C 3 N 3 S 3 ] (x = 1, 2) Groups3A universal synthetic strategy for noncentrosymmetric lead oxyhalide frameworks with strong second-harmonic generation0Achieving an optimal performance balance in UV nonlinear optical crystals via hydrogen-bond regulation1Cation-dominated second-harmonic generation in chiral tetrahydro-1-naphthylammonium halides0Crystal structures and optical properties of two layered lead halide phosphites Pb 3 (HPO 3 )Cl 4 ·H 2 O and Pb 3 (HPO 3 ) 2 Cl 2 ·H 2 O0The condensation of π-conjugated units: a new paradigm for designing high-performance optical crystals4Protonation‐Triggered Structural Transformations in 4‐Hydroxypyridinium Halides for Solar‐Blind UV Functional Crystals3Protonation‐Triggered Structural Transformations in 4‐Hydroxypyridinium Halides for Solar‐Blind UV Functional Crystals8Hydrogen‐Bond‐Modulated Alignment of Iminodiacetic Acid Cations for Achieving Ultraviolet Second Harmonic Generation6Overcoming the Bandgap‐Birefringence Trade‐Off: Proton‐Transfer Engineering of High‐Performance Ultraviolet‐Transparent Organic Crystal5Rigid‐Flexible Coupling Units Enable Robust Large Birefringence2Control of Symmetry and Photophysical Properties of Hybrid Antimony Chlorides via Mixed Organic Cations0(C 2 N 4 H 7 S)(H 2 PO 3 ): Optical Properties Study of a Metal‐Free Amidinothiourea Phosphite0Charge and structural flexibility of tartrate groups enable high-performance ultraviolet nonlinear optical crystals0

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  1. A novel 2-(aminomethyl)pyridineH 2 PO 4 crystal with second-order nonlinear optical performance

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  2. Cooperative Enhancement of Second Harmonic Generation in an Organic–Inorganic Hybrid Antimony Halide

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  3. New Low-Dimensional Lead-Free Perovskite (2-AMP)2BiX7·H2O (X = Cl, Br) Crystals: Synthesis, Stability, and Nonlinear Optical Properties

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  4. BaSb(H2PO2)3Cl2: An excellent UV nonlinear optical hypophosphite exhibiting strong second-harmonic generation response

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  5. SbHPO3F: 2D van der Waals Layered Phosphite Exhibiting Large Birefringence

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  6. Finding a Deep‐UV Borate BaZnB4O8 with Edge‐sharing [BO4] Tetrahedra and Strong Optical Anisotropy

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  9. Phosphites: A Nonlinear Optical Materials System with a Wide Band Gap and Moderate Second-Harmonic Generation Effect

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  10. K 3 C 6 N 7 O 3 ·2H 2 O: A Multifunctional Nonlinear Optical Cyamelurate Crystal with Colossal π-Conjugated Orbitals

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  11. Homochiral Metallohelicates Based on Zinc(II) and Cadmium(II) Clusters with Excellent Thermostability and Remarkable Second-Harmonic Generation

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  12. Characteristics of structure, thermal stability and optical properties for a novel NLO crystal (C5H12NO)H2PO4

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  13. (C 5 H 6.16 N 2 Cl 0.84 )(IO 2 Cl 2 ): a birefringent crystal featuring unprecedented (IO 2 Cl 2 ) − anions and π-conjugated organic cations

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  14. A UV solar-blind nonlinear optical crystal with confined π-conjugated groups

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  16. Compounds consisting of coplanar π-conjugated B3O6-typed structures: An emerging source of ultraviolet nonlinear optical materials

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  17. Solvent-free synthesis of magnesium phosphite-oxalates that show second-harmonic generation responses

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  19. Pb2Cl2(HPO3)(H2O) and Pb3Br2(HPO3)2: Two Phosphite Halides with 3D Structural Networks and Enlarged Birefringence

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  31. Rational Design of Noncentrosymmetric Organic–Inorganic Hybrids with a π-Conjugated Pyridium-Type Cation for High Nonlinear-Optical Performance

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  32. (C 3 N 6 H 7 )BF 4 ·H 2 O and (C 3 N 6 H 7 )SO 3 CH 3 ·H 2 O with large birefringence induced by coplanar π-conjugated [C 3 N 6 H 7 ] + groups

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  33. [(C 5 H 6 N 2 ) 2 H](Sb 4 F 13 ): a polyfluoroantimonite with a strong second harmonic generation effect

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  34. Crystal clear: unveiling giant birefringence in organic–inorganic cocrystals

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  35. Designing promising ultraviolet (UV) birefringent crystals with different hydrogen-bonded phosphate frameworks

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  36. Large optical anisotropy in noncentrosymmetric phosphate with pseudo 2D intercalated layer

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  37. Recent advances in rational structure design for nonlinear optical crystals: leveraging advantageous templates

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  38. Research progress in optical materials with cationic organic planar π-conjugated groups containing CN bonds

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  39. Synthesis and Characterization of Metal Iso-cyamelurate K0.5In0.5(H2C6N7O3)2·9H2O with Large Birefringence

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  40. Designing Optical Anisotropy: Silver-Aminoalkylpyridine Nitrate Complexes with Tunable Structures

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  42. (C8H6BrN2O)NO3: A Hybrid Nonlinear Optical Crystal With an Appropriate Birefringence

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  43. Centric Sc(HPO3)(H2PO3)(H2O) and Acentric Sc(H2PO3)3: Two Ultraviolet Scandium Phosphite Optical Crystals

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  44. A Noncentrosymmetric Metal‐Free Borophosphate: Achieving a Large Birefringence and Excellent Stability by Covalent‐Linkage

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  45. Tunable Optical Anisotropy in Rare‐Earth Borates with Flexible [BO3] Clusters

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  46. C9H7NBrX (X = Cl, Br, NO3): Three Excellent Birefringent Crystals with Distinct Optical Anisotropy Regulated by Anions

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