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RESEARCH PAPER · Chemistry of Materials · 2021

Guanidinium Fluorooxoborates as Efficient Metal-free Short-Wavelength Nonlinear Optical Crystals

Congcong Jin, Hao Zeng, Feng Zhang, Haotian Qiu, Zhihua Yang, Miriding Mutailipu, Shilie Pan

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Guanidinium Fluorooxoborates as Efficient Metal-free Short-Wavelength Nonlinear Optical CrystalsOriginal[C 3 N 6 H 7 ] 2 [B 3 O 3 F 4 (OH)]: a new hybrid birefringent crystal with strong optical anisotropy induced by mixed functional units85[C(NH 2 ) 3 ] 2 S 2 O 8 : combining delocalized and localized π-conjugate units to achieve strong optical anisotropy21Engineering hydrogen bonding to align molecular dipoles in organic solids for efficient second harmonic generation31Li 3 [Al(PO 4 ) 2 (H 2 O) 1.5 ] and Na[AlP 2 O 7 ]: from 2D layered polar to 3D centrosymmetric framework structures8Na 3 B 6 O 10 (HCOO): an ultraviolet nonlinear optical sodium borate-formate33Na 4 Ga 8 S 14 : a Ga-enriched wide band gap ternary alkali-metal sulfide with unique [Ga 12 S 42 ] 12-membered rings2Performance of optical materials with the derivative of planar π-conjugated groups: Recent advances and future prospects37Two porous-layered borates built by B 7 O 13 (OH) clusters and AlO 4 /GaO 4 tetrahedra7New Self-Organizing Optical Materials and Induced Polymorphic Phases of Their Mixtures Targeted for Energy Investigations17Chiral Ligand‐Driven Systematic Synthesis of Coordination Polymers with Non‐centrosymmetric Structures12Driving Nonlinear Optical Activity with Dipolar 2-Aminopyrimidinium Cations in (C4H6N3)+(H2PO3)−115Strong Nonlinearity Induced by Coaxial Alignment of Polar Chain and Dense [BO3] Units in CaZn2(BO3)212Strong Nonlinearity Induced by Coaxial Alignment of Polar Chain and Dense [BO3] Units in CaZn2(BO3)2212Noncentrosymmetric Rare-Earth Borate Fluoride La2B5O9F3: A New Ultraviolet Nonlinear Optical Crystal with Enhanced Linear and Nonlinear Performance48Second-Harmonic Generation-Positive Na 2 Ga 2 SiS 6 with a Broad Band Gap and a High Laser Damage Threshold14A Theoretical Perspective to Study the Optical Properties of Tetrafluoroborates4Organic–Inorganic Hybrid Noncentrosymmetric (Morpholinium) 2 Cd 2 Cl 6 Single Crystals: Synthesis, Nonlinear Optical Properties, and Stability43Structural Characterization and ORR Activity of a Copper Complex Borate and an Unexpected [Ni(atta)(SO4)0.5]+ Borate-Sulfate7Three Co-based tartratoborates with fundamental building blocks [B(C4H2O6)2]5− from facile condensation reactions2Difluoro(oxalato)borates as Short-Wavelength Optical Crystals with Bifunctional [BF 2 C 2 O 4 ] Units38NaB3O4F(OH): A Hydroxyfluorooxoborate with One-Dimensional Chain Featuring Large Birefringence and Short Ultraviolet Cutoff Edge5C(NH2)3Rb(I3O8)(IO3)(I2O6H2): An unprecedented organic–inorganic hybrid polyiodate with two different polyiodate groups13KC9H5O6(H2O): A Promising UV Nonlinear-Optical Material with Large Birefringence Based on a π-Conjugated (C9H5O6)−Group11New Low-Dimensional Lead-Free Perovskite (2-AMP)2BiX7·H2O (X = Cl, Br) Crystals: Synthesis, Stability, and Nonlinear Optical Properties27(C4H10NO)PbX3 (X = Cl, Br): Design of Two Lead Halide Perovskite Crystals with Moderate Nonlinear Optical Properties35Exploring Short-Wavelength Phase-Matching Nonlinear Optical Crystals by Employing KBe2BO3F2 as the Template95Na 2 (C 4 O 4 )(H 3 BO 3 )(H 2 O) 4 ·H 3 BO 3 : the first borate-squarate with strong SHG response obtained by superior synergy11Noncentrosymmetric versus Centrosymmetric: Halogen Induced Variable Coordination Modes of Sn2+ and Structural Transition in Sn3B3O7X (X = Cl and Br)17Cs[B 3 O 3 F 2 (OH) 2 ]: discovery of a hydroxyfluorooxoborate guided by selective organic–inorganic transformation13Deep-ultraviolet nonlinear-optical crystal BaNa2[PO3(OH)]2 with large birefringence and strong second-harmonic-generation response8Discovery of SrZn 2 B 6 O 12 with an unprecedented quadruple-layered configuration0Enhancing birefringence of non-π-conjugated sulfate systems through rare-earth metal-centered polyhedra10Hydroxyfluorooxoborate (NH 4 )[C(NH 2 ) 3 ][B 3 O 3 F 4 (OH)] for exploring the effects of cation substitution on structure and optical properties26K 5 [B 3 O 3 F 4 (OH)] 2 (NO 3 ): the first hydroxyfluorooxoborate-nitrate with a short ultraviolet cutoff edge and large birefringence18LiCs 3 AlB 7 O 14 : achieving enhanced optical anisotropy via [AlO 4 ] tetrahedron introduction to rearrange the anionic framework5Recent progress in borate-based short-wavelength nonlinear optical crystals with boron–oxygen skeleton modification28Recent progress on sulfide infrared nonlinear optical materials with large SHG response and wide band gap26The solvent effect on the morphology and molecular ordering of benzothiadiazole-based small molecule for inkjet-printed thin-film transistors4Synthesis and Spectroscopic Properties of Selected Acrylic and Methacrylic Derivatives of 2-Mercaptobenzothiazole2Identifying Ordered OH/F Anions in Hydroxyfluorides by a Terahertz Spectroscopic Approach21Structural Insights into Layered Tetrahalocuprates(II) Based on Small Unsaturated and Cyclic Primary Ammonium Cations3A new benzothiazolium-based organic nonlinear optical material DABT9Red-Emitting Tetraphenylethylene-Based Boron Thioketonates: Effect of Substitution and Study of Nonlinear Optical Properties7Recent progress of newly developed functional building units and corresponding nonlinear optical materials14“Cation Activation”: An Effective Strategy for the Enhancement of Birefringence36Target-Oriented Synthesis of Borate Derivatives Featuring Isolated [B3O3] Six-Membered Rings as Structural Features20Achieving the full-wavelength phase-matching for efficient nonlinear optical frequency conversion in C(NH2)3BF4513The unexpected salamo-type copper(II) complex: Synthesis, structure, theoretical calculations and fluorescence properties33α- and β-(C4H5N2O)(IO3)·HIO3: Two SHG Materials Based on Organic–Inorganic Hybrid Iodates14Heterologous Isomorphic Substitution Induces Optical Property Enhancement for Deep-UV Crystals: a Case in Rb[B3O3F2(OH)2]10A review of the relationship between the structure and nonlinear optical properties of organic-inorganic hybrid materials149Two UV organic-inorganic hybrid antimony-based materials with superior optical performance derived from cation-anion synergetic interactions30High-pressure/high-temperature synthesis of the new boron-rich terbium hydroxyborate Tb3B12O19(OH)72New Organic Nonlinear Optical Pyridinium-Based Hydrate Crystals: Trimethoxy-Induced Noncentrosymmetric Alignment6Fluorination Strategy Towards Symmetry Breaking of Boron‐centered Tetrahedron for Poly‐fluorinated Optical Crystals15Fluorination Strategy Towards Symmetry Breaking of Boron‐centered Tetrahedron for Poly‐fluorinated Optical Crystals70Physicochemical factors that enhance the third order nonlinear susceptibility in nitroanilines and conjugated polyenyne polymers with arylamine substituents1Achieving great optical anisotropy with the well-directed alignment of π-conjugated groups due to hydrogen bonds9A nonlinear optical crystal with deep-ultraviolet transparency and appropriate birefringence achieved using π-conjugated confined [B 3 O 3 F 4 (OH)] 2−14A smart microporous block copolymer membrane containing fluorescent europium complexes reports drug release through fluorescence changes2Discovery of a new bimetallic borate with strong optical anisotropy activated by π-conjugated [B 2 O 5 ] units3Effect of Nonlinear Optical (Nlo) Properties Featuring Donor-Π-Donor Chromophores in the Extended Localised Π-Conjugation Diformyltriphenylamine Disubstituted Chalcone Derivatives0Effect of Nonlinear Optical (Nlo) Properties Featuring Donor-Π-Donor Chromophores in the Extended Localised Π-Conjugation Diformyltriphenylamine Disubstituted Chalcone Derivatives3Galloborates as ultraviolet nonlinear optical crystals: advances and perspectives8NaB(OH) 3 CH 3 : a deep-ultraviolet optical crystal with unprecedented methyl-modified [B(OH) 3 CH 3 ] units6Recent 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 bonds34Strategically designed metal-free deep-ultraviolet birefringent crystals with superior optical properties18LiASi2O5 (A = K, Rb): Effects of cations on crystal structure and optical properties1Exceptional Optical Anisotropy Enhancement Achieved Through Dual‐Ions Cosubstitution Strategy in Novel Hybrid Bismuth Halides23Toward the ultraviolet (UV) or deep-UV nonlinear optical crystals: The combination of π-conjugated planar [XY3] and tetrahedral [XY4]80Where do the Fluorine Atoms Go in Inorganic‐Oxide Fluorinations? A Fluorooxoborate Illustration under Terahertz Light1Where do the Fluorine Atoms Go in Inorganic‐Oxide Fluorinations? A Fluorooxoborate Illustration under Terahertz Light33[C(NH2)3]6Mo7O24: A Guanidinium Molybdate as a UV Nonlinear Optical Crystal with Large Birefringence17[C(NH2)3][B(C2O2H4)2]: An Organic–Inorganic Hybrid Borate Containing Nonlinear-Optical Active Unit [B(C2O2H4)2]− with Solar-Blind-Region Optical Nonlinearity16Sr2[B5O8(OH)]2 ⋅ [B(OH)3] ⋅ H2O: A Strontium Borate That Shows Deep‐Ultraviolet‐Transparent Nonlinear Optical Properties17Enhancement of Birefringence in π-Conjugated Oxyfluorides Achieved via van der Waals Layered Structural Optimization10Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units11A Noncentrosymmetric Metal‐Free Borophosphate: Achieving a Large Birefringence and Excellent Stability by Covalent‐Linkage27Two Hydroxyfluorooxoborates Achieving Deep‐Ultraviolet Cutoff Edges and Moderate Birefringence by Assembling Multi‐Anionic Groups6HgC4H4O6: A mercury tartrate exhibits phase matchable second harmonic generation effect1Enhanced Birefringence in Phosphates via “Two Steps in One”: d0 Transition Metal Regulation and Fluorination Synergistic Strategy7Tunable Optical Anisotropy in Rare‐Earth Borates with Flexible [BO3] Clusters7Na3[Al2B6P4O22(OH)3](H2O)6 and Na3[Al2BP2O11](H2O)0.5: Two Remarkable Complex Aluminum Borophosphates8[C(NH2)3]10(MoO3)10(PO4)2(HPO4)2·5H2O: Synergy effect of multiple functional units results in significant birefringence10Fluorine-driven materials design of novel deep-ultraviolet nonlinear optical crystal materials: Research progress and challenges6[B3O3F4(OH)]2–: A Versatile Hydroxyfluorooxoborate Heteroanion Producing Compounds with Highly Tunable Optical Anisotropy19Noncentrosymmetric Crystal [C10H8NO2]2SiF6·H2O with Large Birefringence12(C3N2H5)B3O3F2(OH)2: Realizing Large Birefringence via a Synergistic Effect between Anion F/OH‐Ratio Optimization and Cation Activation25Cs2Pb(CO3)2: a novel mixed-metal carbonate with rare Pb-C-O one-dimensional chain0Sulfate Derivatives with Heteroleptic Tetrahedra: New Deep‐Ultraviolet Birefringent Materials in which Weak Interactions Modulate Functional Module Ordering61Sulfate Derivatives with Heteroleptic Tetrahedra: New Deep‐Ultraviolet Birefringent Materials in which Weak Interactions Modulate Functional Module Ordering4C6N7(NH2)3·H3PO4: Strong Second Harmonic Generation and Giant Birefringence Benefiting from Amino Substitution Strategy24Hydrogen bond-derived symmetry transformation in hydroxyborates: Converting the nonlinearity from null to active7Achieving the Birefringence Optimization by Methyl Modulation in Organic Nonlinear Optical Crystals15(C10N2H10)(HI2O6)(HIO3)(IO3): A Birefringent Material Featuring Large π-Conjugated Organic Cation and Two Types of Iodate Anions2SbO(OH)2(IO3): The First Polar Sb5+‐Iodate with a Strong Second‐Harmonic Generation Response and a Wide Bandgap8[C3H7N6]3[B3O5(OH)2] and [C3H8N6]4[B12O19(OH)6]: Two Melamine Borates with Large Birefringence13[C(NH2)3]2S2O6: A SBBO-Like Dithionate Crystal with Large Optical Anisotropy14Designing a Heteroleptic Tetrahedral Group with an Ultrahigh Polarizability Anisotropy by Optimizing the Bonding Electrons Activity and Their Distribution14Structural modification of hydroxyborates by adjusting the number of shared oxygen atoms and hydroxyl groups for further performance enhancement1Nonlinear optical (NLO) properties of donor-π-donor featuring diformyltriphenylamine chalcone derivatives15[C(NH 2 ) 3 ] 2 [C 2 H 5 (C 2 O 4 )]Cl: rational design of a metal-free UV birefringent crystal through the synergistic assembly of three distinct motifs5A strongly birefringent sulfate crystal with a wide second-harmonic generation phase-matching range4An excellent ultraviolet nonlinear optical crystal derived from the polar methylphosphonate unit8BaAlPO 4 F 2 : structure and properties of the first barium fluoroaluminophosphate with the mixed anion group [Al 2 PO 8 F 5 ]1CN 4 H 7 B 3 O 3 F 2 (OH) 2 : short-wave UV hydroxyfluorooxyborate crystals with large birefringence2From poor-active to high performance via heteroleptic tetrahedra engineering: rational design of non-π-conjugated hybrids for phase-matchable ultraviolet nonlinear optics12Optimizing optical anisotropy in low-dimensional structures via intralayer hydrogen bonding modulation and anionic substitution17新型非线性光学晶体和双折射晶体的研究进展（特邀）4Electron density distribution in bis(guanidinium) disodium hypodiphosphate heptahydrate, (CH 6 N 3 ) 2 Na 2 (P 2 O 6 )·7H 2 O1Birefringence Modulation by Phenyl and Acyl Groups in Urea-Based Crystals3(3‐C6H10N2)ZnX4 (X = Cl and Br): Two Excellent UV Nonlinear Optical Crystals Designed by Combination of π‐conjugated and [ZnX4]2− Tetrahedral Units26Designed Metal‐Free Quasi‐1D Crystals with Giant Birefringence8Hydrogen‐Bonded Assembly of Functional Units for Constructing Linear and Nonlinear Optical Crystals10Investigation of Optical Properties and Biological Activities of Antimony(III) Halide Templated by 2,2′-Bipyridinium for Optoelectronic Devices5[CON3H6BF4]: An Efficient Metal‐Free Borate with Optimized Birefringence Achieved by Structural Design Strategy15Non-equivalent terminating roles of hydroxyl and fluorine in hydroxy/fluorooxo-borate optical functional materials2Polar Lithium l -Aspartate Monohydrate: A Semiorganic Ultraviolet Transparent Nonlinear Optical Crystal1[C( NH2 )3] 2SiF6 : Design of Deep Ultraviolet Crystals with Large Birefringence Based on a Fluorination‐Oriented Strategy13Three-In-One: A Guanidinium-Containing Niobium Oxyfluoride with a Perovskite-like Structure Revealing Multifunctional Optical Properties2Four Benzoguanamine-Based Birefringent Crystals with Excellent Optical Anisotropy5Synergistic Design of UV Nonlinear Optical Crystals: Harnessing Flexible π-Conjugated Anions and Guanidinium Cations for Enhanced Performance4Borosilicates as deep-ultraviolet transparent nonlinear optical crystals: Structural motifs, performance limits and future directions9Organic Halogen Substitution-Driven Halogen Bonding Induces Polar 3D Supramolecular Framework and Second-Harmonic-Generation Response7Triple Integration of π‐Conjugated Building Blocks: Unprecedented Assembly for Large Optical Anisotropy11Remarkable Birefringence Enhancement Enabled by π-Conjugated Cyanoguanidine Group Based on Anisotropic Molecule Coordination Approach8Cationic‐Dual‐Modulated Linear and V‐Shaped Birefringent‐Active Unit Generates Remarkable Birefringence6A multi-scale birefringence modulation strategy in DUV/UV crystals induced by organic cations1Targeted hydroxyl fluorination for first-principles design of deep-ultraviolet nonlinear optical crystals: multi-property optimization & chromatic dispersion modulation in Li 2 CsB 7 O 10 F 41The condensation of π-conjugated units: a new paradigm for designing high-performance optical crystals4基于太赫兹光谱技术的硼酸氟化机理分析（特邀）0Hydrogen‐Bond‐Directed Assembly of Urea Derivatives: Exceptional Birefringence Achieved by π ‐Conjugated Unit Alignment3Record‐High Birefringence with Ultralow Dichroic Loss Realized by Cation‐Templated Engineering Ordered Assembly of Linear Birefringent‐Active Unit6Toward the vacuum-ultraviolet frontier in nonlinear optical frequency conversion: phase-matching mechanisms across dimensions and architectures2Exceptional Solar‐Blind Birefringence Engineered by Complementary Hydrogen‐Bond Ordering of π‐Conjugated Units0Designing Novel Solar‐Blind Ultraviolet Nonlinear Optical Crystals Based on Local Proton Distribution Complementary Effect0Designing Novel Solar‐Blind Ultraviolet Nonlinear Optical Crystals Based on Local Proton Distribution Complementary Effect0Structural-Dynamic Synergy in Hydrogen-Bond Reconfiguration Enables Room-Temperature Tunable Nonlinear Optical Materials0Fluorination‐Driven Molecular Polarization Engineering in Hydroxyfluorooxoborates for Generating Strong Short‐Wavelength Nonlinear Optical Responses0

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  33. Hydroxyfluorooxoborate (NH 4 )[C(NH 2 ) 3 ][B 3 O 3 F 4 (OH)] for exploring the effects of cation substitution on structure and optical properties

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