吖啶橙 | 494-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 吖啶橙
• 中文别名: 3,6-2(二甲基胺)ㄚ啶；溶剂橙15
• 英文名称: acridine orange
• 英文别名: 3,6-bis(dimethylamino)acridine；acridine orange base；3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine
• CAS: 494-38-2
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: DPKHZNPWBDQZCN-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C (dec.)(lit.)
• 沸点：
  469℃
• 密度：
  1.169
• 闪点：
  237℃
• 溶解度：
  DMF：2mg/mL； DMSO：20mg/mL；乙醇：0.3mg/mL； PBS（pH 7.2）：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 致癌物分类

国际癌症研究机构致癌剂：蒽醌橙

IARC Carcinogenic Agent:Acridine orange

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第16卷（1978年）一些芳香胺及其相关硝基化合物 - 染发剂、着色剂和杂项工业化学品

IARC Monographs:Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

来源:International Agency for Research on Cancer (IARC)

安全信息

• WGK Germany：
  3
• RTECS号：
  AR7600000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  库房应保持通风、低温和干燥，并与其他食品原料分开存放。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Acridine Orange base
CAS-No. : 494-38-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Solvent Orange 15
3,6-Bis(dimethylamino)acridine
Formula : C17H19N3
Molecular Weight : 265,35 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 165 °C - dec.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
Laboratory experiments have shown mutagenic effects.
Carcinogenicity
This product is or contains a component that is not classifiable as to its carcinogenicity based on its IARC,
ACGIH, NTP, or EPA classification.
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion
May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes
May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: AR7600000

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：有毒物品

• 毒性分级：高毒
• 急性毒性：皮下-小鼠 LD50: 250 毫克/公斤
• 可燃性危险特性：可燃；燃烧产生有毒氮氧化物烟雾
• 储运特性：库房通风、低温干燥；与食品原料分开存放

灭火剂：

• 干粉
• 泡沫
• 沙土
• 二氧化碳
• 雾状水

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3,6-bis(dimethylamino)acridine-9(10H)-thione	36177-74-9	C17H19N3S	297.424
  ——	3,6-bis(N,N-dimethylamino)-9-anilinoacridine	——	C23H24N4	356.47
  吖啶	Acridin	260-94-6	C13H9N	179.221

反应信息

• 作为反应物：
  描述：

  吖啶橙 在 sulfur 作用下， 反应 0.5h， 以94%的产率得到3,6-bis(dimethylamino)acridine-9(10H)-thione
  参考文献：
  名称：

  新型a啶染料分子结合紫外吸收剂的合成，表征及光物理性质的研究

  摘要：

  含紫外线吸收剂的新型a啶有机体（AO）的合成，是通过将AO染料1和3,6-双（二甲基氨基）ac啶-9（10H）-硫酮与（2-羟基-4-（3-碘丙氧基）苯基）（苯基）甲酮。这些染料通过1 HNMR，13 CNMR，HRMS进行表征，研究了在不同溶剂中溶剂变色效应的光物理性质以及商业commercial啶橙和我们合成的染料2-3的pH效应（从2到10）。此外，我们已经计算了它们的吸收，荧光最大值，摩尔消光系数和斯托克斯位移。此外，已将辐照和耐光性稳定性研究与商业染料1和合成染料2-3进行了比较。使用吸收，荧光光谱。由于分子中存在紫外线吸收剂，因此与染料1相比，我们合成的染料2–3在曝光照射光时表现出出色的稳定性。此外，使用高斯09程序的DFT计算计算可为结果提供支持。

  DOI：

  10.1016/j.dyepig.2021.109391
• 作为产物：
  描述：

  2,4,6-三叔丁基苯酚 以 乙腈 为溶剂， 生成 吖啶橙
  参考文献：
  名称：

  吖啶橙的光致质子耦合电子转移反应：综合光谱和动力学分析

  摘要：

  吖啶橙 ((3)*AO) 的三重激发态在乙腈中与三叔丁基苯酚 ((ttb)PhOH) 发生质子耦合电子转移 (PCET) 反应。每个反应组分都具有光谱特征，这为通过瞬态吸收光谱并行监测单个质子转移、电子转移和 H(•)-转移组分提供了难得的机会。这种增强的光学跟踪以及激发态热化学分析有助于确定激发态 PCET 反应性的机制。(3)*AO 通过协同质子-电子转移 (CPET) 从 (ttb)PhOH 猝灭形成吖啶自由基 (AOH(•)) 和 (ttb)PhO(•) (kCPET = 3.7 × 10(8) M( -1) s(-1)，KIE = 1.3)。随后，AOH(•) 还原苯氧基自由基 (kET = 5.5 × 10(9) M(-1) s(-1))，形成 AOH(+) 和 (ttb)PhO(-)，

  DOI：

  10.1021/ja505755k
• 作为试剂：
  描述：

  DL-赖氨酸 在 lysine decarboxylase 、 吖啶橙 、 cucurbituril 作用下， 生成 1,5-二氨基戊烷
  参考文献：
  名称：

  底物选择性超分子串联测定：通过杯芳烃和葫芦脲大环化合物的荧光染料置换监测精氨酸酶和二胺氧化酶的酶抑制作用

  摘要：

  适度选择性的主客体结合与令人印象深刻的酶转化特异性相结合，可以实时监测均相溶液中的酶反应。所得酶测定（“超分子串联测定”）利用荧光染料与大环宿主的动态结合，与底物和产物的结合竞争。研究了两个酶促反应的例子：精氨酸酶催化的精氨酸水解为鸟氨酸和二胺氧化酶将尸胺氧化为 5-氨基戊醛，其中底物对大环化合物的亲和力高于产物（“底物选择性测定法” ”）。底物的消耗使荧光染料在酶促反应过程中进入大环，这导致所需的荧光响应。对于精氨酸酶，使用对磺化杯[4]芳烃作为大环化合物，其与精氨酸的结合常数为 6400 M(-1)，与鸟氨酸的结合常数为 550 M(-1)，与选定的荧光结合常数为 60,000 M(-1)染料（1-氨基甲基-2,3-二氮杂双环[2.2.2]辛-2-烯）；该染料在其络合状态下显示出较弱的荧光，这导致在酶促反应过程中关闭荧光响应。对于二胺氧化酶，葫芦[7] uril (CB7) 用作大环，显示结合常数为

  DOI：

  10.1021/ja904165c

文献信息

• Trifunctional^99mTc based radiopharmaceuticals: metal-mediated conjugation of a peptide with a nucleus targeting intercalator
  作者：Karel Zelenka、Lubor Borsig、Roger Alberto

  DOI：10.1039/c0ob00504e

  日期：——

  The development of molecular imaging agents with multiple functions has become a major trend in radiopharmaceutical chemistry. We present herein the syntheses of trifunctional compounds, combining an acridine orange (AO) based intercalator with a GRP receptor specific bombesin like peptide (BBN). Metal-mediated conjugation of these two functions via the [2 + 1] approach to the third function, the [M(CO)3]+ (M = 99mTc, Re) moiety, yielded the final trifunctional molecules. The strongly fluorescent acridine orange, a nuclear targeting agent, has been derivatised with 4-imidazolecarboxylate as a bidentate ligand and bombesin with an isonitrile group as a monodentate ligand. For cell and nuclear uptake studies, [Re(L1-BBN)(L2-Ical)(CO)3] type complexes were synthesized and characterized. For radiopharmaceutical purposes, the 99mTc analogues have been prepared in a stepwise synthesis. Fluorescence microscopy studies on PC-3 cells, bearing the BBN receptor, showed high and rapid uptake into the cytoplasm. For the bifunctional molecule, lacking the BBN peptide, no internalization was observed.

  多功能分子成像剂的发展已成为放射性药物化学的主要趋势。本文介绍了三功能化合物的合成，这些化合物结合了以吖啶橙（AO）为基础的插入剂和GRP受体特异性类似bombesin的肽（BBN）。通过[2 + 1]方法，将这两种功能与第三种功能[M(CO)3]+（M = 99mTc，Re）部分进行金属介导的连接，得到了最终的三功能分子。作为核靶向剂，吖啶橙具有强烈的荧光，衍生化为双齿配体4-咪唑羧酸酯，bombesin则带有异氰基作为单齿配体。为了研究细胞和核摄取，我们合成了并表征了[Re(L1-BBN)(L2-Ical)(CO)3]型配合物。为了放射性药物的目的，我们采用逐步合成法合成了99mTc类似物。对携带BBN受体的PC-3细胞进行荧光显微镜研究，结果显示细胞质中的摄取率高且迅速。对于缺乏BBN肽的双功能分子，未观察到内化现象。
• Chemodosimeter for Selective and Sensitive Chromogenic and Fluorogenic Detection of Mustard Gas for Real Time Analysis
  作者：Vinod Kumar、Hemlata Rana、G. Raviraju、Arvind K. Gupta

  DOI：10.1021/acs.analchem.7b04882

  日期：2018.1.16

  Since the first use of chemical warfare agents (CWA) (1915) to the recent attacks in Syria (2017) on mankind, there have been many incidents where CWA have claimed thousands of lives and left many more contaminated. In order to provide the appropriate and immediate medical counter measure to the victims, the exact classification of these chemical agents within few minutes on the field itself using a rapid and simple detection technique is extremely important to save the lives of the effected people. This has motivated all of us to explore the novel strategies/detection systems that can be field deployable with better selectivity and greater sensitivity. In view of this, we present a novel chemosensor, 3,6-bis(dimethylamino)-9(10H)-acridine thione (1), that can detect mustard gas and its simulant by both chromogenic and fluorogenic methods. For the first time, a single probe was able to demonstrate the detection with unprecedented selectivity over most probable interferences (nerve agents and alkylating agents) including solvents, acids, and bases which are routinely present in the environment. The desired level of sensitivity by naked eyes (0.04 mg/mL), UV spectroscopy (0.02 mg/mL), and fluorescence spectroscopy (0.005 mg/mL) makes this method truly field deployable. For the spot detection on the affected areas, a handy and potable chemosensor kit was also fabricated. This paper provides a simple, highly specific, and easy to use method in “actual sense” that not only detects the agents in the solution phase but also in the contaminated samples.

  自1915年首次使用化学战剂(CWA)到2017年针对人类的叙利亚最近袭击以来，CWA已经造成了许多事件，夺去了数千人的生命，并使更多的人受到污染。为了向受害者提供适当的即时医疗对策，在现场几分钟内使用快速简便的检测技术对这些化学剂进行精确分类对于拯救受影响的人们生命至关重要。这激励我们所有人探索新颖的策略/检测系统，这些系统可以在现场部署时具有更好的选择性和更高的灵敏度。鉴于此，我们提出了一种新型化学传感器，3,6-双(二甲基氨基)-9(10H)-吖啶硫酮(1)，可以利用色原性和荧光性方法检测芥子气及其模拟物。首次，单个探针能够在包括环境中有规律存在的溶剂、酸和碱在内的最可能干扰物(神经剂和烷化剂)中展现前所未有的选择性检测。通过裸眼(0.04 mg/mL)、UV光谱(0.02 mg/mL)和荧光光谱(0.005 mg/mL)能够实现所需水平的灵敏度，从而真正实现现场部署。为了在受影响区域进行点检测，还制备了一种便携式的化学传感器工具箱。本文提供了一种简单、高度特定且易于使用的方法，不仅可以检测溶液相中的化学剂，还可以检测受污染样品中的化学剂。
• [EN] METHODS AND COMPOSITIONS USING REPAIR CELLS AND CATIONIC DYES<br/>[FR] MÉTHODES ET COMPOSITIONS UTILISANT DES CELLULES RÉPARATRICES ET DES COLORANTS CATIONIQUES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2017019832A1

  公开（公告）日：2017-02-02

  This disclosure describes compositions and methods for delivering and localizing repair cells to therapeutic targets.

  这份披露描述了将修复细胞传递和定位到治疗靶点的组合物和方法。
• NOVEL DYES WITH PHOSPHINIC ACID, PHOSPHINATE, PHOSPHONATE AND PHOSPHONAMIDATE SUBSTITUENTS AS AUXOCHROMIC GROUPS AND METHODS FOR PREPARING THE SAME
  申请人：Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e. V.

  公开号：US20180223102A1

  公开（公告）日：2018-08-09

  Compounds of formula I are disclosed: wherein X 1 , X 2 , X 3 , X 4 are independently H, F, Cl, Br, I, CN, NO 2 , OR 1 , SR 1 , NR 1 R 2 , COR 1 , COOR 1 , CONR 1 R 2 , PO 3 R 1 R 2 , SO 2 R 1 , SO 3 R 1 or R 3 ; R 1 and R 2 are, e.g., H, alkyl or aryl or optionally a ring; R 3 is, e.g., alkyl, alkenyl, alkynyl, aryl or cycloalkyl; Y is OR 1 , NR 1 R 2 , or NR 1 R 3 ; Q is O, S, SO 2 , NR, C(R 3 ) 2 , Si(R 3 ) 2 , Ge(R 3 ) 2 , P(═O)R 3 or P(═O)OR 3 ; Q and X 1 can optionally form part of a ring; L and M are independently OR 1 , SR 1 , NR 1 R 2 and R 3 ; L and M can optionally form part of a ring; Z is O, S, NR 1 , CR 1 R 3 or aryl; and Z and X 4 can optionally form part of a ring.

  式I的化合物已被披露： 其中X1、X2、X3、X4独立地为H、F、Cl、Br、I、CN、NO2、OR1、SR1、NR1R2、COR1、COOR1、CONR1R2、PO3R1R2、SO2R1、SO3R1或R3；R1和R2为H、烷基或芳基或可选地为环；R3为烷基、烯基、炔基、芳基或环烷基；Y为OR1、NR1R2或NR1R3；Q为O、S、SO2、NR、C(R3)2、Si(R3)2、Ge(R3)2、P(═O)R3或P(═O)OR3；Q和X1可选择地形成环的一部分；L和M独立地为OR1、SR1、NR1R2和R3；L和M可选择地形成环的一部分；Z为O、S、NR1、CR1R3或芳基；Z和X4可选择地形成环的一部分。
• Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid‐Photoredox Hybrid Catalyst for the Generation of <i>α</i> ‐Carbonyl Radicals
  作者：Sanju Das、Tanumoy Mandal、Suman De Sarkar

  DOI：10.1002/adsc.202101053

  日期：2022.2.15

  A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic

  据报道，一种易于获得的有机-无机杂化催化剂用于α-卤代羰基化合物的还原断裂。稳健的杂化催化剂是 ZnCl 2 Lewis 酸和吖啶橙作为光活性有机染料的自稳定组合。已经使用光物理和电化学实验详细研究了这种混合催化剂的机械特性。一项系统的研究使我们能够发现合适的路易斯酸以有效地稳定α-卤代羰基化合物，从而降低标准有机染料范围内的还原电位。该策略通过引导光氧化还原循环通过氧化猝灭途径解决了脱卤氢化或烷基自由基同源偶联等问题。光活性有机染料和路易斯酸对应物之间的协同作用通过有效和受控地生成烷基自由基，使功能化与广泛的偶联伙伴成为可能，并作为昂贵的后过渡金属基光催化剂的合适替代品。为了证明这种协同催化体系的应用潜力，研究了四种不同的α-羰基溴的合成转化，具有广泛的底物范围。

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