卤代有机物（HOCs）广泛存在于地表和工程水体中。这类有机物质包括人工合成化学品以及氯化消毒和自然卤化过程中生成的副产物。相较于非卤代有机物，HOCs具有更强的持久性、生物累积性和毒性，其在水环境中的转化和归趋是环境科学研究的热点。光化学降解（包括直接光解和间接光解）是影响HOCs在水环境中归趋和持久性的重要非生物转化途径。本研究选取对氯间二苯酚（PCMX）和双酚S（BPS）及其卤代衍生物作为研究对象，系统开展实验室和自然阳光光解实验，综合光谱学表征、光解动力学探究、光产物鉴定和模型构建，旨在阐明卤素取代基如何影响它们的光物理性质和光化学活性。

研究表明，在废水氯化消毒过程中，PCMX与HOCl发生亲电取代反应，导致氯代副产物的生成（Cl-PCMX、2Cl-PCMX）。在环境水平溴离子（Br^-）的存在下，卤代产物以溴代衍生物为主（Br-PCMX、2Br-PCMX）。由于卤素取代基的红移和重原子效应，卤代衍生物呈现出更强的光吸收特性和光反应活性。在中性pH条件下，四种卤代PCMX的B吸收带相较于母体分别红移了10、30、11和33 nm。在UV₂₅₄辐照条件下，光量子产率遵循2Br-PCMX（0.52 mol E^-1）> Br-PCMX（0.14 mol E^-1）> 2Cl-PCMX（0.11 mol E^-1）> Cl-PCMX（0.09 mol E^-1）> PCMX（0.04 mol E^-1）的规律。特别地，二卤代产物比单卤代产物更具光反应性。PCMX及其卤代衍生物的光转化途径包括光羟基化（+ OH）、光还原脱卤化（- X）和光亲核取代。生态毒性评估表明，卤代衍生物比母体PCMX具有更高的持久性、生物累积性和毒性。本研究结果加深了我们对PCMX在氯化消毒过程中的转化以及其卤代衍生物在后续紫外消毒过程或阳光照射水体中光化学行为的理解。

卤取代基也显著改变了BPS的物理化学和光化学性质。光谱滴定结果显示，四氯双酚S（TCBPS，4.16）和四溴双酚S（TBBPS，4.13）的pK_a值比BPS（7.85）小约3.7个单位，表明卤代衍生物在环境相关pH条件下主要以酚阴离子形式存在。卤素取代基还导致TCBPS和TBBPS的吸收光谱相对于BPS发生了显著的红移，从而增强了卤代衍生物对阳光光子的吸收。同时，TCBPS和TBBPS的量子产率远高于BPS，这归因于卤取代基的重原子效应有利于系内窜越（ISC）生成三重激发态进而发生光致脱卤化反应。GCSOLAR模型预测表明，在天气晴朗、仲秋正午阳光辐照下，BPS、TCBPS和TBBPS在南京地区（32°2′7.3′′N, 118°50′21′′E）地表水中的近表层半衰期分别为810.2、3.4和0.7 min。毒性预测结果表明，BPS衍生物物及其光产物可能对水生生物具有潜在生态风险。研究结果表明，在阳光照射的地表水体和紫外线辐射的废水介质中，直接光解是四卤代BPS重要的转化过程。

综上，卤取代基显著改变了PCMX和BPS的光物理性质，卤取代基的红移效应和重原子效应在PCMX和BPS的光归趋过程中扮演重要角色。本研究深化了对HOCs在水环境中的光反应活性和光化学行为的认识，为精准评估HOCs的环境持久性和人体暴露风险提供了理论依据和实验数据。

Halogenated organic compounds (HOCs) are widely present in surface and engineered aquatic environments. These HOCs include artificial synthesis chemicals, as well as byproducts generated from chlorination disinfection and natural halogenation processes. HOCs have stronger persistence, bioaccumulation, and toxicity compared to their unsubstituted organic compounds and their transformation and fate in aquatic environments are hotspots of environmental science research. Photochemical degradation, including direct and indirect photolysis, is an important abiotic pathway affecting the fate and persistence of HOCs in aquatic environments. Herein, we selected chloroxylenol (PCMX) and bisphenol S (BPS) as parent compounds, systematically conducted the laboratory and natural sunlight photolysis experiments, integrating spectroscopic characterization, photolytic kinetics investigation, identification of photoproducts, and model construction, aiming to elucidate how halogen substituents affect their photophysical properties and photochemical reactivity.

Results indicate that chlorination of PCMX mainly proceeded through electrophilic substitution to give chlorinated products, including Cl-PCMX and 2Cl-PCMX. The presence of environmental bromide (Br^-) resulted in brominated analogues (Br-PCMX and 2Br-PCMX). Due to the bathochromic and heavy atom effects of halogen substituents, these products show increased light absorption and photoreactivity. At neutral pH, the B bands of the four halogenated PCMX were red-shifted by 10, 30, 11, and 33 nm, respectively, as compared to their parent one. Under UV₂₅₄ radiation, the quantum yields (mol E^-1) followed the order of 2Br-PCMX (0.52) > Br-PCMX (0.14) > 2Cl-PCMX (0.11) > Cl-PCMX (0.09) > PCMX (0.04). Particularly, di-halogenated products are more photochemically reactive than mono-halogenated ones.The photolytic mechanisms of PCMX and its halogenated products include photohydroxylation (+OH), photoreductive dehalogenation (-X), and photonucleophilic substitution. Ecotoxicity evaluation suggest that these halo-derivatives have higher persistence, bioaccumulation, and toxicity than the parent PCMX. Results of this contribution advance our understanding of the transformation of PCMX during chlorination and the photochemical activity of its halogenated derivatives in subsequent UV disinfection process or sunlit surface waters.

Halogen substituents significantly alter the physicochemical properties of BPS. Spectroscopic titration results indicated that the pK_a of TCBPS (4.16) and TBBPS (4.13) are approximately 3.7 units smaller than that of BPS (7.85), indicating that the halogenated derivatives are mainly present as the phenolate anions under circumneutral conditions. The halogen substituents also cause a significant bathochromic shift in the absorption spectra of TCBPS and TBBPS compared to BPS, leading to the enhanced absorption of sunlight. Meanwhile, TCBPS and TBBPS showed higher quantum yields than BPS, which can be attributed to the heavy atom effect of halogen substituents, favoring the generation of the triplet excited state through intersystem crossing (ISC) and subsequent undergo photodehalogenation reaction. GCSOLAR modeling predicted half-lives for BPS, TCBPS, and TBBPS in surface water in Nanjing (32°2′7.3′′N，118°50′21′′E) under noon sunlight in clear mid-autumn days as 810.2, 3.4, and 0.7 min, respectively. Toxicity evaluation suggested

BPS derivatives and their photoproducts may pose potential ecological risks to aquatic organisms. Our findings highlight direct photolysis as an important mechanism accounting for the attenuation of tetrahalogenated bisphenols in both sunlit surface waters and UV based water treatment processes.

Overall, halogen substitutes significantly alter the photophysical properties of PCMX and BPS. The bathochromic and heavy atom effect of halogen substituents play an important role on the photo-fate of PCMX and BPS. This study deepens the understanding of photoreactivity and photochemical behavior of HOCs in aquatic environments, providing guidance and experimental data for accurately evaluating the environmental persistence and human exposure risks of HOCs.

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