Name: synthesis of plant phenol-derived polymeric dyes for direct or mordant-based hair dyeing
Uploaded: 2016-12-01T12:00:00.000+00:00
Duration: 9 min 46 s
Description: Watch this Scientific Journal Video about Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing at JoVE.com

This work was supported by the New Professor Research Foundation Program, funded by Gyeongsang National University (Grant Number 2015-04-020).

공장 페놀 유래 고분자 염료의 1. 준비 <ol><li> 100 mM의 아세트산 나트륨 완충액 (pH 5.0) 및 무수 에탄올 8 ㎖를 32 ㎖의 카테킨 수화물 (0.1 g) - 카테 콜 (0.1 g) 및 (+) 녹인다. </li><li> T. 10 mg을 추가 catechol-과 카테킨 함유 버퍼에 베르의 락카. 격렬하게 혼합 사각형 페트리 접시에 솔루션을 붓는다. 24 시간 동안 진탕 배양기 (25 회전)에 실온에서 접시를 품어. 짙은 검정색 투명의 용액의 색상의 극적인 변화는 락카 유도 커플 링 반응 후 육안으로 관찰 할 수있다. </li><li> 불용성 고분자 입자를 스핀 다운하기 위해 20,000 XG에서 10 분 동안 솔루션을 원심 분리기. 더 탈염에 대한 깊은 블랙 뜨는을 사용합니다. </li><li> 5 kDa의 한외 여과 디스크와 반응 액을 탈염. 한외 여과 내지 20 ㎖의 반응 부피를 농축 한 후, 증류수 300 ㎖에 첨가하여, 반응 완충액을 교환. 마지막으로, 여과하여, 25 ㎖의 상기 용액의 부피를 농축시킨다. </li></ol> 회색 케라틴 헤어 2. 염색 솔루션 <ol><li> 다음 여섯 가지 폴리머 솔루션을 준비 : 고분자 염료, 고분자 염료 / 다음날에 FeSO4, 고분자 염료 / 다음날에 FeSO4의 pH 3 물, 고분자 염료 / 다음날에 FeSO4 pH를 11 물, 고분자 염료 / 병용했을 아세트산 4, 및 고분자 염료 / 병용했을 암모니아 4. <ol><li> 중합체 염료, 탈염 중합체 염료 (1.4) 1 ㎖ 증류수 5 mL를 섞는다. </li><li> 매염제 솔루션의 단계 2.1.1에서 혼합물에 다음날에 FeSO4의 0.33 g을 추가합니다. 격렬하게 소용돌이 완전히 다음날에 FeSO4를 용해한다. </li><li> pH를 3 ~ 11 수용액의 경우, 1 N 염산 또는 1 N의 NaOH를 사용하여 5 ㎖의 증류수의 pH를 조정한다. 그런 다음 탈염 고분자 염료 (1.4) 다음날에 FeSO4의 0.33 g 1 ㎖를 추가합니다. </li><li> 아세트산 산성 또는 암모니아 처리 솔루션의 경우, GL 1.0 ㎖의 혼합acial 아세트산 또는 증류수 5 mL를 암모니아수 용액 1.0. 그런 다음 탈염 고분자 염료 (1.4) 다음날에 FeSO4의 0.33 g 1 ㎖를 추가합니다. </li></ol></li><li> 의 머리를 흡수하기 위해, 또는 다음날에 FeSO4의 0.33 g없는 증류수 6 ml의에 카테킨 수화물 (0.1 g) - 식물 단량체를 들어, 카테 콜 (0.1 g) 및 (+)를 섞는다. </li><li> 즉시 단계 2.1 및 2.2에서 염색 솔루션이 준비 될 때, 완전히 솔루션에서 5 cm 긴 회색 머리카락 다발 (0.2 g)을 흡수. 2.5 시간 동안 진탕 배양기 (160 RPM)에서 32 ° C에서 머리 다발을 품어. </li><li> 그 후, 모발 다발을 꺼내 흐르는 물로 씻어. 습기를 제거하기 위해 전자 헤어 드라이어를 사용합니다. 중합체 염료에 의한 색상의 변화를 육안으로 가시화 될 수있다. <ol><li> 색 파라미터를 얻기 위해 (즉, L *, a * 및는 B *), 제조자의 프로토콜에 따라 종래의 색채를 채용한다. 머리 t을 구겨따라서 이들을 색채의 렌즈로 측정 될 수 있도록 공으로 resses. 색도계 렌즈와 머리의 다른 지역에이 과정을 반복합니다. </li><li> 각 염색 머릿 일곱 번 컬러의 파라미터를 측정한다. 평균 및 매개 변수의 표준 편차를 계산합니다. 식을 사용하여 ΔE를 계산한다 : [(100 - L의 *) 2 + (a *) 2 + (b *) 2] 1/2. </li></ol></li></ol> 3. 색상 내구성 테스트 <ol><li> 40ml의 증류수에 황산 도데 실 나트륨 (SDS) 200 mg을 용해. 실온에서 5 분간 SDS 함유 물에 완전히 염색 된 모발을 담근다. 머리 다발을 꺼내 한 후 세제를 제거하기에 충분한 수돗물로 씻어. 습기를 제거하기 위해 전자 헤어 드라이어를 사용합니다. </li><li> 색 파라미터를 얻기 위해 (즉, L *, a * 및 B는 *)에 따른 manufactur의 종래의 색채를 채용어의 프로토콜입니다. 같은 염색 머리를 한 번 더 단계 3.1에 설명 된 균열을 반복 한 후 다시 매개 변수를 측정합니다. </li><li> 증류수 40 ㎖에 800 mg의 SDS를 녹인다. 단계 3.1에 기재된 바와 같이, 더욱 동일한 염색 된 머리 회 침지 반복한다. 전반적으로, SDS 용액을 4 회 총 염색 각 머리칼을 치료. </li></ol>

<ol>
	<li>Jeon, J. R., Chang, Y. S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Laccase-mediated+oxidation+of+small+organics:+bifunctional+roles+for+versatile+applications.">Laccase-mediated oxidation of small organics: bifunctional roles for versatile applications.</a> Trends Biotechnol. 31, 335-341 (2013).</li><li>Kudanga, T., Nyanhongo, G. S., Guebitz, G. M., Burton, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Potential+applications+of+laccase-mediated+coupling+and+grafting+reactions:+a+review.">Potential applications of laccase-mediated coupling and grafting reactions: a review.</a> Enzyme Microb Technol. 48, 195-208 (2011).</li><li>Jeon, J. R., Le, T. T., Chang, Y. S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Dihydroxynaphthalene-based+mimicry+of+fungal+melanogenesis+for+multifunctional+coatings.">Dihydroxynaphthalene-based mimicry of fungal melanogenesis for multifunctional coatings.</a> Microb. Biotechnol. 9, 305-315 (2016).</li><li>Jeon, J. R., Baldrian, P., Murugesan, K., Chang, Y. S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Laccase-catalyzed+oxidations+of+naturally+occurring+phenols:+From+in+vivo+biosynthetic+pathways+to+green+synthetic+application.">Laccase-catalyzed oxidations of naturally occurring phenols: From in vivo biosynthetic pathways to green synthetic application.</a> Microb. Biotechnol. 5, 318-332 (2012).</li><li>Chung, K. T., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Mutagenicity+and+toxicity+studies+of+p-phenylenediamine+and+its+derivatives.">Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives.</a> Toxicol. Lett. 81, 23-32 (1995).</li><li>Bai, Y. H., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=p-aminophenol+and+p-phenylenediamine+induce+injury+and+apoptosis+of+human+HK-2+proximal+tubular+epithelial+cells.">p-aminophenol and p-phenylenediamine induce injury and apoptosis of human HK-2 proximal tubular epithelial cells.</a> J. Nephrol. 25, 481-489 (2012).</li><li>Jeon, J. R., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Laccase-catalyzed+polymeric+dye+synthesis+from+plant-derived+phenols+for+potential+application+in+hair+dyeing:+Enzymatic+colorations+driven+by+homo-+or+hetero-polymer+synthesis.">Laccase-catalyzed polymeric dye synthesis from plant-derived phenols for potential application in hair dyeing: Enzymatic colorations driven by homo- or hetero-polymer synthesis.</a> Microb. Biotechnol. 3, 324-335 (2010).</li><li>Franca, S. A., Dario, M. F., Esteves, V. B., Baby, A. R., Velasco, M. V. R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Types+of+hair+dye+and+their+mechanisms+of+action.">Types of hair dye and their mechanisms of action.</a> Cosmetics. 2, 110-126 (2015).</li><li>Ball, V., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Deposition+mechanism+and+properties+of+thin+polydopamine+films+for+high+added+value+applications+in+surface+science+at+the+nanoscale.">Deposition mechanism and properties of thin polydopamine films for high added value applications in surface science at the nanoscale.</a> BioNanoSci. 2, 16-34 (2012).</li><li>Barrett, D. G., Sileika, T. S., Messersmith, P. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Molecular+diversity+in+phenolic+and+polyphenolic+precursors+of+tannin-inspired+nanocoatings.">Molecular diversity in phenolic and polyphenolic precursors of tannin-inspired nanocoatings.</a> Chem. Commun. 50, 7265-7268 (2014).</li><li>Sileika, T. S., Barrett, D. G., Zhang, R., Lau, K. H. A., Messersmith, P. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Colorless+multifunctional+coatings+inspired+by+polyphenols+found+in+tea,+chocolate,+and+wine.">Colorless multifunctional coatings inspired by polyphenols found in tea, chocolate, and wine.</a> Agnew. Chem. 52, 10766-10770 (2013).</li><li>Boonsong, P., Laohakunjit, N., Kerdchoechuen, O. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Natural+pigments+from+six+species+of+Thai+plants+extracted+by+water+for+hair+dyeing+product+application.">Natural pigments from six species of Thai plants extracted by water for hair dyeing product application.</a> J. Clean. Prod. 37, 93-106 (2012).</li><li>Bechtold, T., Turcanu, A., Ganglberger, E., Geissler, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Natural+dyes+in+modern+textile+dyehouses+-+how+to+combine+experiences+of+two+centuries+to+meet+the+demands+of+the+future.">Natural dyes in modern textile dyehouses - how to combine experiences of two centuries to meet the demands of the future.</a> J. Clean. Prod. 5, 499-509 (2003).</li><li>Zheng, H., Gao, C., Peng, B., Shu, M., Che, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=pH-responsive+drug+delivery+system+based+on+coordination+bonding+in+a+mesostructured+surfactant/silica+hybrid.">pH-responsive drug delivery system based on coordination bonding in a mesostructured surfactant/silica hybrid.</a> J. Phys. Chem. C. 115, 7230-7237 (2011).</li><li>Robbins, C. R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=.">.</a> Chemical and physical behavior of human hair. , 105-176 (2011).</li></ol>

The authors declare that they have no competing financial interests.

흥미롭게도, 우리의 방법은 천연 페놀의 산화제에 의한 중합와 각질 머리를 염색하는 데 걸린 시간을 감소시켰다. 그것은 또한 pH를 변경하고 매염제인가와 중합체 염료의 간단한 조작을 통해 머리에 다양한 색상을 유도. 식물 페놀의 락카 - 촉매 산화와 각질 머리의 현장 배양에 효과적인 염색 (7)를 달성하기 위해 지나치게 긴 배양 시간이 필요합니다. 느린 ?...

Laccases는 페놀과 폴리 페놀 화합물 대한 활성 옥시 다제이다. 그들은 식물, 균류, 곤충, 박테리아 등 다양한 생물에서 발견되었습니다. 그들의 효소 활동은 여러 형태 발생 현상 일에 기여한다. 효소는 또한 작은 유기물을 고체 표면에 결합되는 라디칼의 형성의 결과로, 기판의 단 전자 산화 촉매. 이러한 커플 링 프로세스는 올리고머 및 폴리머의 합성으로 이어질 및 락카 기판은 식물 페놀과 같은 천연 소스에서 경우 3., 효소 반응이 녹색 화학에 대해 큰 관심의 관능 2, 표면. 여기, 두 반응물과 촉매는 천연 자원으로부터 있습니다. 또한, 얻어진 제품은 전체 반응은 천연 페놀의 생체 내 합성 모방 때문에 식물 리그닌, 폴리 (flavono 중합체를 포함한 상기 천연물 유사한ID)와 상기 부식 - 작은 식물 페놀 화합물 고도로 가교 다제 - 유도 라디칼 커플 4이다. 식물 유래의 페놀 락카 - 촉매 커플 링 반응에서 파생 된 제품은 현장에서 배양 백발을 통해 염색하는데 사용될 수 있고 대안으로 시판 한 염료로 개발 될 수있다. 상업적 헤어 염색 에이전트 피의 -phenylenediamine (PPD)에 기초하기 때문에 이러한 대안은 중요 PPD 관련 디아민 화합물, 수소, 유독성 발암 것으로 나타났다 옥사이드, 인간 5, 6 알러지.에서 락카 - 촉매 커플 링 반응은 laccases 식물 페놀 기능적 각각 과산화수소 및 P의 -phenylenediamine 7 대체. 그러나, 락카 기반 시스템의 염색 속도가 상업용 하나보다 훨씬 느리다. 일반적으로, PPD 계 염색 제제는 달성 한 시간 미만을 필요각질 머리에 효과적인 색상 변경은 락카 기반 반응이 하룻밤 배양 (7)를 필요로한다. 느린 동역학 염색은 두 가지 현상을 설명 할 수있다. 첫째, 낮은 pH 완충의 사용 (예를 들어, pH가 5) 락카 제 활성을 최대화하기 위해, 따라서 매트릭스에 염료의 깊은 침투를 억제 케라틴 매트릭스 부종의 정도를 감소하는 것으로 관찰되었다. 실제로, pH가 높은 상태에서 진행 염색 반응을 허용 화제는 상업적 모발 염색 제품 (8)에 통합 될 것으로 나타났다. 둘째, 중합 반응 동안 케라틴 표면에 강한 흡수를 나타내는 발색단 가능한 분자의 개수는 배양 시간 (중합 예 정도)에 비례하는 것으로 밝혀졌다. 예를 들어, 도파민 polydopamine로의 변환은 흑색 (9)의 형성에 수반되었다 많은 표면에 강한 접착을 유도하는 것으로 나타났다. &lt;/ P&gt; 현재의 연구에서, T.에서 얻은 고분자 제품을 미리은 합성 카테킨과 카테 콜 락카 - 촉매 산화 베르 염색 각질 머리를 치료하는 데 사용되었다. 우리는 중합체의 흡착 능력은 모노머 식물 페놀보다 훨씬 더 강할 것이라는 그들은 초기에 저 분자량 올리고머를 형성하는 것으로 가정 하였다. 결과는 프리 - 합성 폴리머를 사용하는 경우, 효소 산화력이 더 이상 필요했던 것을 입증 없다. 이것은 pH가 조절 될 수 있고 그 금속 이온은 효소 활성에 관계없이, 헤어 염색 치료에 사용될 수 있음을 나타낸다. 이 프로토콜은 친환경 및 신 재생 식물 유래 페놀 (그림 1)을 사용하는 동안 색상의 다양 한 음영에서 각질 머리를 염색하는 간단하고 빠른 방법을 제공한다.

<table><tbody><tr><td>Sodium dodecyl Sulfate</td><td>Promega</td><td>H5114</td><td></td></tr><tr><td>Laccase from Trametes versicolor</td><td>Sigma</td><td>38429-1G</td><td>Enzyme activity is denoted as 0.53 U/mg</td></tr><tr><td>(+)-catechin hydrate</td><td>Sigma</td><td>C1251-5G</td><td></td></tr><tr><td>1,2-dihydroxybenzene (catechol)</td><td>Sigma</td><td>135011-5G</td><td></td></tr><tr><td>Ammonia water&amp;nbsp;</td><td>Duksan</td><td>701</td><td>Ammonia contents is denoted as 25 ~ 30%</td></tr><tr><td>Acetic acid, glacial</td><td>Duksan</td><td>448</td><td></td></tr><tr><td>Iron(II) sulfate heptahydrate</td><td>JUNSEI</td><td>83380-1250</td><td></td></tr><tr><td>Ultracell 5 kDa</td><td>Amicon</td><td>PLCC06210</td><td></td></tr><tr><td>Stirred ultrafiltration cells</td><td>Millipore</td><td>Model 8200</td><td></td></tr><tr><td>Human gray hair</td><td>PheonixKorea</td><td>Not available</td><td></td></tr><tr><td>Colorimeter</td><td>SPEC</td><td>JCS-10</td><td></td></tr><tr><td>Square dish</td><td>SPL</td><td>10125</td><td>125 * 125 * 20 (mm)</td></tr></tbody></table>

synthesis of plant phenol-derived polymeric dyes for direct or mordant-based hair dyeing

식물 페놀의 곰팡이 락카 - 촉매 중합의 제품과 각질 머리의 현장 배양에 통해 효과적인 머리 염색은 이전에 증명되었다. 그러나, 염색 처리는 모발 염색 상용 제품에 비해 완료하는 데 오랜 시간이 걸린다. 이러한 병목 현상을 극복하기 위해, 또는 매염제 제제 (예를 들면, 다음날에 FeSO4), 여기에서 다양한 색상 및 색조 영구 케라틴 모발 염색을 달성하기 위해 사용 하였다없이 어느 카테킨 및 카테 콜의 락카 베르 Trametes의 산화 반응의 중합체 제품, 중고 합성 . 산성 아세트산 나트륨 완충액에서 락카 동작 식물 페놀과 반응 후 결합 깊은 흑색 착색되었다. 착색 염료 제품은 탈염 및 한외 여과로 농축시켰다. 또는 매염제 에이전트없이 염료, 회색 머리카락 위스콘신 ΔE 값 (즉, 색차 값)의 상당한 증가를 야기얇은 2.5 시간. 또한, 다른 케라틴 색상 및 색조가 매염하여 pH 변화에 따라 유도 하였다. 염색 머리는 또한 우리의 방법은 영원한 머리 염색을 야기 할 수 있음을 나타냅니다, 세제 처리에 강한 저항성을 나타냈다. 전반적으로, 우리의 작업은 상업 독성 디아민 계 염료에 대한 대안으로 환경 친화적 인 헤어 염색 방법을 개발에 새로운 통찰력을 제공하고있다 .

우선, 중합체 염료의 염색 능력은 식물 유래의 단량체 (예, 카테킨, 및 카테 콜)의 것과 비교 하였다. 모발의 타고난 그레이 색 (데이터 미도시) 식물 단량체 매우 안정적으로 유지하면서 고분자 염료 회색 모발 케라틴 (도 2a 및도 3)의 색상에 큰 변화를 야기. 고분자 제품의 염색 능력에 에이전트를 매염의 효과는 다음 평가 하였...

Watch this Scientific Journal Video about Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing at JoVE.com

Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing

Here, we present a protocol to use pre-synthesized polymeric products derived from fungal laccase-catalyzed polymerization of plant phenols, either with or without mordant agents (e.g., FeSO4), to induce detergent-resistant keratin hair dyeing within 2.5 hours.

직접 또는 모던 기반 머리 염색에 대한 공장 페놀 유래 고분자 염료의 합성

Effective hair dyeing through in situ incubation of keratin hair with the products of fungal laccase-catalyzed polymerization of plant phenols has been ...

synthesis-plant-phenol-derived-polymeric-dyes-for-direct-or-mordant

Research

JoVE Journal

Chemistry

9.2K 조회수.  Gyeongsang National University. Here, we present a protocol to use pre-synthesized polymeric products derived from fungal laccase-catalyzed polymerization of plant phenols, either with or without mordant agents (e.g., FeSO4), to induce detergent-resistant keratin hair dyeing within 2.5 hours.

비디오: Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Functionalized naphthalenes have applications in a variety of research fields ranging from the synthesis of natural or biologically active molecules to the preparation of new organic dyes. Although numerous strategies have been reported to access naphthalene scaffolds, many procedures still present limitations in terms of incorporating functionality, which in turn narrows the range of available substrates. The development of versatile methods for direct access to substituted naphthalenes is therefore highly desirable.
The Diels-Alder (DA) cycloaddition reaction is a powerful and attractive method for the formation of saturated and unsaturated ring systems from readily available starting materials. A new microwave-assisted intramolecular dehydrogenative DA reaction of styrenyl derivatives described herein generates a variety of functionalized cyclopenta[b]naphthalenes that could not be prepared using existing synthetic methods. When compared to conventional heating, microwave irradiation accelerates reaction rates, enhances yields, and limits the formation of undesired byproducts.
The utility of this protocol is further demonstrated by the conversion of a DA cycloadduct into a novel solvatochromic fluorescent dye via a Buchwald-Hartwig palladium-catalyzed cross-coupling reaction. Fluorescence spectroscopy, as an informative and sensitive analytical technique, plays a key role in research fields including environmental science, medicine, pharmacology, and cellular biology. Access to a variety of new organic fluorophores provided by the microwave-assisted dehydrogenative DA reaction allows for further advancement in these fields.

Microwave-assisted intramolecular dehydrogenative Diels-Alder (DA) reactions provide concise access to functionalized cyclopenta[b]naphthalene building blocks. The utility of this methodology is demonstrated by one-step conversion of the dehydrogenative DA cycloadducts into novel solvatochromic fluorescent dyes via Buchwald-Hartwig palladium-catalyzed cross-coupling reactions.

작용 Naphthalenes / Solvatochromic의 염료의 합성을위한 전자 레인지를 이용한 분자 Dehydrogenative Diels-앨더 반응

Functionalized naphthalenes have applications in a variety of research fields ranging from the synthesis of natural or biologically active molecules to ...

연구

화학

Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

We demonstrate a method for high-throughput catalyst screening using a parallel pressure reactor starting from the initial synthesis of a nickel &#945;-diimine ethylene polymerization catalyst. Initial polymerizations with the catalyst lead to optimized reaction conditions, including catalyst concentration, ethylene pressure and reaction time. Using gas-uptake data for these reactions, a procedure to calculate the initial rate of propagation (kp) is presented. Using the optimized conditions, the ability of the nickel &#945;-diimine polymerization catalyst to undergo chain transfer with diethylzinc (ZnEt2) during ethylene polymerization was investigated. A procedure to assess the ability of the catalyst to undergo chain transfer (from molecular weight and 13C NMR data), calculate the degree of chain transfer, and calculate chain transfer rates (ke) is presented.

A protocol for the high-throughput analysis of polymerization catalyst, chain transfer polymerizations, polyethylene characterization, and reaction kinetic analysis is presented.

병렬 반응기 압력 및 연쇄 이동 중합 키네틱 분석을 사용하여 에틸렌 중합

We demonstrate a method for high-throughput catalyst screening using a parallel pressure reactor starting from the initial synthesis of a nickel ...

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

A method for the synthesis of electroactive polymers is demonstrated, starting with the synthesis of extended conjugation monomers using a three-step process that finishes with Negishi coupling. Negishi coupling is a cross-coupling process in which a chemical precursor is first lithiated, followed by transmetallation with ZnCl2. The resultant organozinc compound can be coupled to a dibrominated aromatic precursor to give the conjugated monomer. Polymer films can be prepared via electropolymerization of the monomer and characterized using cyclic voltammetry and ultraviolet-visible-near infrared (UV-Vis-NIR) spectroscopy. Nanoparticles (NPs) are prepared via emulsion polymerization of the monomer using a two-surfactant system to yield an aqueous dispersion of the polymer NPs. The NPs are characterized using dynamic light scattering, electron microscopy, and UV-Vis-NIR-spectroscopy. Cytocompatibility of NPs is investigated using the cell viability assay. Finally, the NP suspensions are irradiated with a NIR laser to determine their effectiveness as potential materials for photothermal therapy (PTT).

A protocol is presented for the synthesis and preparation of nanoparticles consisting of electroactive polymers.

전기 활성 고분자 나노 입자 출전 광열 등록

A method for the synthesis of electroactive polymers is demonstrated, starting with the synthesis of extended conjugation monomers using a three-step ...

공학

Genetic Incorporation of Biosynthesized L-dihydroxyphenylalanine (DOPA) and Its Application to Protein Conjugation

L-dihydroxyphenylalanine (DOPA) is an amino acid found in the biosynthesis of catecholamines in animals and plants. Because of its particular biochemical properties, the amino acid has multiple uses in biochemical applications. This report describes a protocol for the genetic incorporation of biosynthesized DOPA and its application to protein conjugation. DOPA is biosynthesized by a tyrosine phenol-lyase (TPL) from catechol, pyruvate, and ammonia, and the amino acid is directly incorporated into proteins by the genetic incorporation method using an evolved aminoacyl-tRNA and aminoacyl-tRNA synthetase pair. This direct incorporation system efficiently incorporates DOPA with little incorporation of other natural amino acids and with better protein yield than the previous genetic incorporation system for DOPA. Protein conjugation with DOPA-containing proteins is efficient and site-specific and shows its usefulness for various applications. This protocol provides protein scientists with detailed procedures for the efficient biosynthesis of mutant proteins containing DOPA at desired sites and their conjugation for industrial and pharmaceutical applications.

Genetic Incorporation of Biosynthesized L-dihydroxyphenylalanine DOPA and Its Application to Protein Conjugation

Here, we present a protocol for the genetic incorporation of L-dihydroxyphenylalanine biosynthesized from simple starting materials and its application to protein conjugation.

Biosynthesized L-dihydroxyphenylalanine (DOPA) 및 단백질 활용의 응용의 유전 결합

L-dihydroxyphenylalanine (DOPA) is an amino acid found in the biosynthesis of catecholamines in animals and plants. Because of its particular biochemical ...

생화학

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

We report a procedure to linearly scale-up the synthesis of 2,8-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzothiophene-S,S-dioxide (compound 4) and 2,8-bis(10H-phenothiazin-10-yl)dibenzothiophene-S,S-dioxide (compound 5) using Buchwald-Hartwig cross-coupling reaction conditions. In addition, we demonstrate a scaled-up synthesis of all non-commercially available starting materials that are required for the amination cross-coupling reaction. In the present article, we provide the detailed synthetic procedures for all of the described compounds, alongside their spectral characterization. This work shows the possibility to produce organic molecules for optoelectronic applications on a large scale, which facilitates their implementation into real world devices.

Scale-up synthesis of highly efficient thermally activated delayed fluorescence emitters is described in the presented article.

스케일-업 Dibenzothiophene S, S-이산화 코어에 따라 열 활성화 지연된 형광 방출의 화학 합성

We report a procedure to linearly scale-up the synthesis of 2,8-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzothiophene-S,S-dioxide (compound 4) and ...

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds

Cyclic voltammetry (CV) is a technique used in the analysis of organic compounds. When this technique is combined with electron paramagnetic resonance (EPR) or ultraviolet-visible and near-infrared (UV-Vis-NIR) spectroscopies, we obtain useful information such as electron affinity, ionization potential, band-gap energies, the type of charge carriers, and degradation information that can be used to synthesize stable organic electronic devices. In this study, we present electrochemical and spectroelectrochemical methods to analyze the processes occurring in active layers of an organic device as well as the generated charge carriers.

In this article, we describe electrochemical, electron paramagnetic resonance, and ultraviolet-visible and near-infrared spectroelectrochemical methods to analyze organic compounds for application in organic electronics.

사용 하 여 순환 Voltammetry, UV-Vi-NIR, EPR Spectroelectrochemistry 유기 화합물 분석

Cyclic voltammetry (CV) is a technique used in the analysis of organic compounds. When this technique is combined with electron paramagnetic resonance ...

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Methine-bridged conjugated bicyclic aromatic compounds are common constituents of a range of biologically relevant molecules such as porphyrins, dipyrrinones, and pharmaceuticals. Additionally, restricted rotation of these systems often results in highly to moderately fluorescent systems as observed in 3H,5H-dipyrrolo[1,2-c:2',1'-f]pyrimidin-3-ones, xanthoglows, pyrroloindolizinedione analogs, BODIPY analogs, and the phenolic and imidazolinone ring systems of Green Fluorescent Protein (GFP). This manuscript describes an inexpensive and operationally simple method of performing a Claisen-Schmidt condensation to generate a series of fluorescent pH dependent pyrazole/imidazole/isoindolone dipyrrinone analogs. While the methodology illustrates the synthesis of dipyrrinone analogs, it can be translated to produce a wide range of conjugated bicyclic aromatic compounds. The Claisen-Schmidt condensation reaction utilized in this method is limited in scope to nucleophiles and electrophiles that are enolizable under basic conditions (nucleophile component) and non-enolizable aldehydes (electrophile component). Additionally, both the nucleophilic and electrophilic reactants must contain functional groups that will not inadvertently react with hydroxide. Despite these limitations, this methodology offers access to completely novel systems that can be employed as biological or molecular probes.

The Claisen-Schmidt condensation reaction is an important methodology for the generation of methine-bridged conjugated bicyclic aromatic compounds. Through utilizing a base-mediated variant of the aldol reaction, a range of fluorescent and/or biologically relevant molecules can be accessed through a generally inexpensive and operationally simple synthetic approach.

claisen-슈미트 응축 접근법을 이용한 pH 의존피라졸, 이미다졸, 이소인돌론 디피리네 플루오로포레스의 합성

Methine-bridged conjugated bicyclic aromatic compounds are common constituents of a range of biologically relevant molecules such as porphyrins, ...

Quantitative 31P NMR Analysis of Lignins and Tannins

The development of sustainable biorefinery products is confronted, among others, with the challenge of lignin and tannin valorization. These abundant, renewable aromatic biopolymers have not been widely exploited due to their inherent structural complexity and high degrees of variability and species diversity. The lack of a defined primary structure for these polyphenols is further compounded with complex chemical alterations induced during processing, eventually imparting a large variety of structural features of extreme significance for any further utilization efforts.
Consequently, a protocol for the rapid, simple, and unequivocal identification and quantification of the various functional groups present in natural polyphenols, is a fundamental prerequisite for understanding and accordingly tailor their reactivity and eventual utility.
Quantitative 31P NMR offers the opportunity to rapidly and reliably identify unsubstituted, o-mono substituted, and o-disubstituted phenols, aliphatic OHs, and carboxylic acid moieties in lignins and tannins with broad application potential.
The methodology consists of an in situ quantitative lignin or tannin labeling procedure using a suitable 31P containing probe, followed by the acquisition of a quantitative 31P NMR spectrum in the presence of an internal standard. The high natural abundance of the 31P nucleus allows for small amounts of the sample (~30 mg) and short NMR acquisition times (~30-120 min) with well-resolved 31P signals that are highly dependent on the surrounding chemical environment of the labeled OH groups.

Quantitative 31P NMR Analysis of Lignins and Tannins

31P NMR is a powerful tool for the structural elucidation of polyphenols. This fast, easy, precise, quantitative, and highly reproducible analytical procedure, that allows for the quantification and differentiation of the different types of hydroxy, phenolic, and carboxylic groups in lignins and tannins has now become a routine analytical tool.

리닌과 탄닌의 정량적 31P NMR 분석

The development of sustainable biorefinery products is confronted, among others, with the challenge of lignin and tannin valorization. These abundant, ...

섬유 인증을 위한 Curcumin의 Photoluminescence를 강화하기 위한 키토산 사용

Enhanced Photoluminescence of Curcuma longa Extracts via Chitosan-Mediated Energy Transfer for Textile Authentication Applications

Dyes for security markings play a pivotal role in safeguarding the integrity of products across various fields, such as textiles, pharmaceuticals, food, and manufacturing among others. However, most commercial dyes used as security markings are costly and may contain toxic and harmful substances that pose a risk to human health. Curcumin, a natural phenolic compound found in turmeric, possesses distinct photoluminescent properties alongside its vibrant yellow color, making it a potential candidate material for authentication applications. This study demonstrates a cost-effective and eco-friendly approach to develop enhanced photoluminescent emissions from curcumin dyes for textile authentication. Curcumin was extracted from C. longa using sonication-assisted-solvent extraction method. The extract was dip-coated and dyed into the textile substrates. Chitosan was introduced as a post-mordanting agent to stabilize the curcumin and as a co-sensitizer. Co-sensitization of curcumin with chitosan triggers energy transfer to enhance its luminescent intensity. The UV-visible absorption peak at 424 nm is associated with the characteristic absorption of curcumin. The photoluminescence measurements showed a broad emission peaking at 545 nm with significant enhancement attributed to the energy transfer induced by chitosan, thus showing great potential as a naturally derived photoluminescent dye for authentication applications.

저자 스포트라이트: Curcumin을 사용한 친환경 축광 섬유 인증

Photoluminescence is one of the most effective authentication mechanisms being used today. Utilizing and enhancing naturally sourced materials with inherent photoluminescent properties and incorporating them into fabric substrates can lead to development of green, sustainable, and functional textiles for smart applications.

섬유 인증 응용 분야를 위한 키토산 매개 에너지 전달을 통한 Curcuma longa 추출물의 향상된 광발광

Dyes for security markings play a pivotal role in safeguarding the integrity of products across various fields, such as textiles, pharmaceuticals, food, ...

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섬유 인증 응용 분야를 위한 키토산 매개 에너지 전달을 통한 Curcuma longa 추출물의 향상된 광발광

섬유 인증 응용 분야를 위한 키토산 매개 에너지 전달을 통한 Curcuma longa 추출물의 향상된 광발광