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RESEARCH PAPER · Angewandte Chemie International Edition · 2022

An Optically Anisotropic Crystal with Large Birefringence Arising from Cooperative π Orbitals

Yanqiang Li, Xu Zhang, Zhou Yang, Weiqi Huang, Yipeng Song, Han Wang, Minjuan Li, Maochun Hong, Junhua Luo, Sangen Zhao

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An Optically Anisotropic Crystal with Large Birefringence Arising from Cooperative π OrbitalsOriginalSn3B10O17Cl2 Achieving Birefringence Enhancement by Stereochemical Activity Lone Pair9K 3 C 6 N 7 O 3 ·2H 2 O: A Multifunctional Nonlinear Optical Cyamelurate Crystal with Colossal π-Conjugated Orbitals44(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 cations56C 10 H 10 ClNO 3 : exploration of birefringent crystals in an isoquinoline system20Design and synthesis of anisotropic crystals with π -conjugated rings toward giant birefringence36Dramatically improved optical anisotropy by realizing stereochemically active lone pairs in a sulfate system, K 2 SO 4 ·HIO 323α-BBO-like π-Conjugated Crystal with Large Birefringence16Recent Development of Sn II , Sb III ‐based Birefringent Material: Crystal Chemistry and Investigation of Birefringence130Recent Development of SnII, SbIII‐based Birefringent Material: Crystal Chemistry and Investigation of Birefringence6Chain‐like [S x ] ( x =2–6) Units Realizing Giant Birefringence with Transparency in the Near‐Infrared for Optoelectronic Materials53Chain‐like [S x ] ( x =2–6) Units Realizing Giant Birefringence with Transparency in the Near‐Infrared for Optoelectronic Materials5A Hydrogen Bonded Supramolecular Framework Birefringent Crystal89A Hydrogen Bonded Supramolecular Framework Birefringent Crystal13Naphthalene-Like Unit That Induces Strong Optical Anisotropy in C10H8NO2Br and C10H8NO2Br·H2O12Quartz‐Like Structure, Optical Activity, and High Stability in the First Chiral Cation‐Coordinated Perovskite Semiconductor11(NH 4 ) 2 (I 5 O 12 )(IO 3 ) and K 1.03 (NH 4 ) 0.97 (I 5 O 12 )(IO 3 ): Mixed‐Valent Polyiodates with Unprecedented I 5 O 12 − Unit Exhibiting Strong Second‐Harmonic Generation Responses and Giant Birefringence22C14H10BrNO2: A Birefringent Crystal with an Expanded π-Conjugated Group13Designing a Dimension Reduced Hybrid Perovskite with Robust Large Birefringence by Expanding Cationic π‐Delocation40Heterologous Isomorphic Substitution Induces Optical Property Enhancement for Deep-UV Crystals: a Case in Rb[B3O3F2(OH)2]10A Two‐Dimensional Hybrid Perovskite With Heat Switching Birefringence47A Two‐Dimensional Hybrid Perovskite With Heat Switching Birefringence7Designing Sulfate Crystals with Strong Optical Anisotropy through π‐Conjugated Tailoring51Designing Sulfate Crystals with Strong Optical Anisotropy through π‐Conjugated Tailoring11Hydroxyl-Driven Enhanced Birefringence in Borophosphates3Achieving strong second harmonic generation effects induced via dimensional increase of PbX 6 octahedra and halogen substitutes in (C 10 H 11 N 3 )PbX 4 (X = Cl or Br)26C 8 H 6 IN 3 O 4 : a birefringent crystal induced by uniformly aligned hybrid groups10Synthesis and Characterization of Metal Iso-cyamelurate K0.5In0.5(H2C6N7O3)2·9H2O with Large Birefringence8A Highly Optical Anisotropic Hybrid Perovskite for Efficient Manipulation of Light Polarization64C9H7NBrX (X = Cl, Br, NO3): Three Excellent Birefringent Crystals with Distinct Optical Anisotropy Regulated by Anions34Intramolecular Hydrogen Bonds Enhance Structure Coplanarity, Resulting in Significant Birefringence in Bridged-Bipyridine Halides7Halogen Bond Unlocks Ultra‐High Birefringence73Halogen Bond Unlocks Ultra‐High Birefringence14C6N7(NH2)3·H3PO4: Strong Second Harmonic Generation and Giant Birefringence Benefiting from Amino Substitution Strategy24A Robust Phosphonate‐Based Hydrogen‐Bonded Organic Framework Birefringent Crystal39Unprecedented Silver‐Based Hybrid Pyroelectric Enabling Wide Spectral Photo‐Pyroelectricity for Birefringence Photomodulation7Unprecedented Silver‐Based Hybrid Pyroelectric Enabling Wide Spectral Photo‐Pyroelectricity for Birefringence Photomodulation1[C8H6BrN2O]Cl and [C8H6IN2O]Cl: Two birefringent crystals with π-conjugated quinazoline groups2(C10N2H10)(HI2O6)(HIO3)(IO3): A Birefringent Material Featuring Large π-Conjugated Organic Cation and Two Types of Iodate Anions2Enhanced Coplanarity and Giant Birefringence in Hydroxypyridinium Nitrate via Hydrogen Bonding between Planar Donors and Planar Acceptors15Enhanced Coplanarity and Giant Birefringence in Hydroxypyridinium Nitrate via Hydrogen Bonding between Planar Donors and Planar Acceptors53Strategically designed anisotropic organic–inorganic metal halides (OIMHs) with superior balance between bandgap and birefringence12[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 range4A tri-alkali/alkaline-earth metal fluorophosphate deep-ultraviolet birefringent crystal with coexisting PO 3 F and PO 2 F 24Synergistic engineering of ultraviolet metal-free crystals with exceptional birefringence via pyridine-derived dimers14Double Sb‐N Coordination Enables Record‐High Birefringence in UV‐Transparent Crystals71Double Sb‐N Coordination Enables Record‐High Birefringence in UV‐Transparent Crystals8Sb2(TeO4)(SO4): An Anhydrous Tellurite Sulfate with Large Birefringence and Enhanced Thermal Stability8Giant Birefringence Enabled by the Highly Anisotropic Linear IX 2 − (X = Cl, Br) Building Blocks6Giant Birefringence Enabled by the Highly Anisotropic Linear IX 2 − (X = Cl, Br) Building Blocks32Bridging the Interlayer Binding to Ordered π‐Conjugated Units for Constructing High‐Performing Light Polarization Crystals8Bridging the Interlayer Binding to Ordered π‐Conjugated Units for Constructing High‐Performing Light Polarization Crystals48Hydrogen‐Bonded Assembly of Functional Units for Constructing Linear and Nonlinear Optical Crystals10[CON3H6BF4]: An Efficient Metal‐Free Borate with Optimized Birefringence Achieved by Structural Design Strategy15All-three-in-one: Pb2(H2PO4)2(C2O4) significantly enhanced birefringence in phosphate materials4Giant 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–Carboxylate24Dual‐Sided Multidentate Coordination Strategy Enables Record Birefringence in UV‐Transparent Antimony‐Based Hybrid Crystals37Dual‐Sided Multidentate Coordination Strategy Enables Record Birefringence in UV‐Transparent Antimony‐Based Hybrid Crystals11CsICl 2 : A Record-Birefringent Inorganic Crystal with Ultrawide Infrared Transparency Enabled by Linear Interhalogen ICl 2 – Units36Giant Birefringence Induced by Intermolecular Aromatic Interactions in Hydrogen‐Bonded Organic Frameworks37From (C12H9N2)2TeBr6·2H2O to (C12H9N2)2TeBr6: Dehydration-Driven Crystal Reorganization for Birefringence Optimization6On-Crystal Spectral Modulator from Polarized Propagation of Lanthanide-Titanium Nanoclusters1Organic π-conjugated units as versatile building blocks for high-performance birefringent crystals6Hybrid Zinc‒Based Halides with Giant Optical Anisotropy via Protonation‒Engineered π ‒Conjugated Organic Group24Achieving 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) Groups3Molecular pseudo-halogen engineering enables remarkable birefringence enhancement in hybrid perovskites0The condensation of π-conjugated units: a new paradigm for designing high-performance optical crystals4Unveiling the Superior Birefringence Property of a Record‐Birefringent Crystal with Unique Building Block12An UV Transparent Metal‐Free Sulfate With Giant Birefringence Enabled by Optimal Structural Anisotropy4Density-Compensated Polarizability Anisotropy for Record Birefringence in Short-Wavelength Ultraviolet Inorganic Crystals11NH 4 B 3 PO 6 (OH) 3 : A Hydroxyborophosphate with Short DUV Cutoff Edge and Large Birefringence2(C 5 H 7 N 2 ) (C 8 H 4 O 4 ) PbBr: Jahn–Teller Distortion‐Induced Tilting of π‐Conjugated Planes Resolving the Second‐Order Polarizability–Structural Anisotropy Conflicts13Record‐High Birefringence with Ultralow Dichroic Loss Realized by Cation‐Templated Engineering Ordered Assembly of Linear Birefringent‐Active Unit6Lock‐and‐Key Assembly Enables Record Birefringence in Monocyclic π‐Conjugated Crystals via Spatial Confinement of Linear Polyhalide5Bio-inspired proton-conformation-coupled hydrogen-bond network reconfiguration for adaptive optical anisotropy0Interlayer Electronic Decoupling Unlocks Giant Birefringence in π‐Conjugated Metal‐Organic Frameworks0Optical phenomena of angular selectivity and nonreciprocity appeared in the layered anisotropic absorption crystal0Designing Novel Solar‐Blind Ultraviolet Nonlinear Optical Crystals Based on Local Proton Distribution Complementary Effect0A Dynamic Hydrogen‐Bonded Organic Framework With Giant OFF–ON Birefringence0

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  1. Sn3B10O17Cl2 Achieving Birefringence Enhancement by Stereochemical Activity Lone Pair

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  2. 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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  3. (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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  4. C 10 H 10 ClNO 3 : exploration of birefringent crystals in an isoquinoline system

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  5. Design and synthesis of anisotropic crystals with π -conjugated rings toward giant birefringence

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  6. Dramatically improved optical anisotropy by realizing stereochemically active lone pairs in a sulfate system, K 2 SO 4 ·HIO 3

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  7. α-BBO-like π-Conjugated Crystal with Large Birefringence

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  8. Recent Development of Sn II , Sb III ‐based Birefringent Material: Crystal Chemistry and Investigation of Birefringence

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  14. Naphthalene-Like Unit That Induces Strong Optical Anisotropy in C10H8NO2Br and C10H8NO2Br·H2O

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  15. Quartz‐Like Structure, Optical Activity, and High Stability in the First Chiral Cation‐Coordinated Perovskite Semiconductor

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  16. (NH 4 ) 2 (I 5 O 12 )(IO 3 ) and K 1.03 (NH 4 ) 0.97 (I 5 O 12 )(IO 3 ): Mixed‐Valent Polyiodates with Unprecedented I 5 O 12 − Unit Exhibiting Strong Second‐Harmonic Generation Responses and Giant Birefringence

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  17. C14H10BrNO2: A Birefringent Crystal with an Expanded π-Conjugated Group

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  18. Designing a Dimension Reduced Hybrid Perovskite with Robust Large Birefringence by Expanding Cationic π‐Delocation

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  19. Heterologous Isomorphic Substitution Induces Optical Property Enhancement for Deep-UV Crystals: a Case in Rb[B3O3F2(OH)2]

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  20. A Two‐Dimensional Hybrid Perovskite With Heat Switching Birefringence

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  22. Designing Sulfate Crystals with Strong Optical Anisotropy through π‐Conjugated Tailoring

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  23. Designing Sulfate Crystals with Strong Optical Anisotropy through π‐Conjugated Tailoring

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  49. Giant Birefringence Enabled by the Highly Anisotropic Linear IX 2 − (X = Cl, Br) Building Blocks

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  50. Giant Birefringence Enabled by the Highly Anisotropic Linear IX 2 − (X = Cl, Br) Building Blocks

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