JP2013522419A - 光学特性が向上した高次構造化色素 - Google Patents
光学特性が向上した高次構造化色素 Download PDFInfo
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- JP2013522419A JP2013522419A JP2013500157A JP2013500157A JP2013522419A JP 2013522419 A JP2013522419 A JP 2013522419A JP 2013500157 A JP2013500157 A JP 2013500157A JP 2013500157 A JP2013500157 A JP 2013500157A JP 2013522419 A JP2013522419 A JP 2013522419A
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- multimer
- organic dye
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- dimer
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
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Abstract
Description
本願は、2010年3月15日出願の米国特許仮出願第61/314,038号に基づくPCT出願でありかつそれに基づく優先権を主張するものである。
〔式中、Rは、ハロゲンまたは−C(O)NR(後者は、タンパク質、核酸などの他の分子に結合させることが可能である)のいずれかであり、かつmおよびpは、S、O、およびNなどのヘテロ原子が含まれうる炭素鎖を示す2〜20の数であり、かつB、C、X、Y、E、G、J、L、さらにはB’、C’、X’、Y’、E’、G’、J’、L’は、それぞれ独立した水素、重水素、またはハロゲン置換基であり、かつZは、CH、N、またはBである〕
でありうる。
〔式中、Rは、ハロゲンまたは−C(O)NR(後者は、タンパク質、核酸などの他の分子に結合させることが可能である)のいずれかであり、かつmおよびpは、S、O、およびNなどのヘテロ原子が含まれうる炭素鎖を示す2〜20の数であり、かつA、B、C、X、Y、E、K、Q、S、T、U、V、W、さらにはB’、C’、X’、Y’、E’、K’、Q’、S’、T’U’V’W’は、それぞれ独立した水素、重水素、またはハロゲン置換基であり、かつZは、CH、N、またはBである〕
架橋は、典型的には、式:A−NH−(CH2)m−C(<CH2>xOR)−(CH2)n−NH−B〔式中、m、n、およびxは、1〜10(好ましくは1〜4)であり、かつRは、COOHまたはその誘導体である〕を有する。架橋は、他のヘテロ原子(すなわち、N、O、S)またはヘテロ環(hetrocycles)を含有可能である。Aおよび(nad)Bは、アルキル基またはアルケニル基である。
大きいRaman断面積で可視〜近IR領域の光を吸収する分子は、材料の核心要素である。本開示の実施例としては、異なる部位の1つ以上の水素原子が重水素で同位体置換された有機色素が挙げられる。有機色素としては、ローダミンやフルオレセインのようなキサンテン色素、クリスタルバイオレットのようなトリアリールメタン色素、ベンゾトリアゾールアゾのようなアゾ色素、メルカプトピリジンが挙げられる。二量体は、カップリング試薬(すなわち、O−(ベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスフェート)の存在下での2つの色素単量体のカップリング反応により取得可能である。それらの色素で利用される同位体置換は、色素形成反応の同位体置換前駆体の使用を介して取得可能である。同位体分子種はまた、二量体への組込み前に重水素化酸性媒体中で色素を加熱することによる発色団の置換活性芳香族プロトンの同位体交換により取得可能である。
MeOHで予浸されたMillipore PVDF膜上にさまざまな濃度(すなわち、1pM、1μM、10μM)のR6G色素誘導体のアリコート(1μlの各サンプル)を吸収させることにより、Ramanスペクトルを記録した。メタノールで予浸されたPVDF膜上に色素材料を充填するためにドットブロット装置を利用した。BBI製の金溶液および銀溶液を用いて膜にコーティングを施した。
膜を完全にインキュベートしうる容積(約5〜10ml)で検体に金ナノ粒子(すなわち、PROTOGOLD、BBI Inc.)を適用する。光から保護するために金溶液中の膜にカバーをかけて、染色が肉眼ではっきり見えるまで低速振盪機(20〜50rpm)上に置いた。金粒子は、ナノ粒子のサイズが20〜40nmの範囲内にある市販のPROTOGOLD溶液でありうる。
染色された色が暗赤色から暗褐色に変化するまで銀増強溶液を適用し、低速振盪(20〜50rpm)させながら一晩乾燥させる。銀粒子は、2つの銀溶液(A:B=1:1、BBI Inc.)を組み合わせることにより、その後の市販の銀増強キット溶液の処理を含めて、社内で作製される。銀粒子サイズの大きさは、通常40nmよりも大きく、銀染色時間は、5分間未満である。
D0−R6G単量体およびD0−R6G二量体のUV吸収スペクトル
D4−R6G単量体(D4=4個のHを重水素化したもの)およびD0−R6G二量体(D0=重水素化していないもの)の可視吸収スペクトルを図2に示す。両方の色素をメタノールに溶解させ、Cary 4 UV−Vis分光光度計でスペクトルを記録した。図2に示されるとおり、R6G二量体のUV吸収スペクトルは、R6G単量体のものと異なる。D4−R6G単量体は、527nmに極大吸収を有するUVスペクトルを示すが、D0−R6G二量体のUVスペクトルは、533nmの極大吸収に加えて明瞭なショルダーを有する。ショルダーは、色素濃度の増加と共により短波長側に広がる。D4−R6G単量体のUV吸収は、いずれの濃度でもショルダーを示さなかった。MeOHに溶解させた場合、R6G二量体は、種々の凝集体を形成する傾向があるが、R6G単量体は、その傾向がない。D0−R6G二量体のショルダーは、色素のさまざまな凝集状態の指標となりうる。D0−R6G二量体のモル吸光係数の計算値は、1.206×106M−1cm−1であり、一方、D4−R6G単量体の計算値は、1.16×105M−1cm−1である。したがって、二量体化により吸光度が1桁増大した。
D0−R6G二量体およびD4−R6G単量体の規格化蛍光発光スペクトルを図3に示す。両方の色素をメタノールに溶解させ、Cary Varian蛍光分光光度計でスペクトルを記録した。蛍光発光ピーク波長で類似の強度値になるようにD0−R6G二量体(10μm)およびD4−R6G単量体(50μm)の濃度を選択し、比較のために重ね合わせた。D0−R6G二量体Ramanシグナル内に明瞭なより低い蛍光ノイズが存在したため、その蛍光強度をチェックしてからそれをD4−R6G単量体のものと比較する必要があった。図3に示されるとおり、D0−R6G二量体は、50μMでのD4−R6G単量体発光(550nmで350)と比較して、10μMでより高い発光吸収(emission absorption)(559nmの450)を有する。D0−R6G単量体の参照蛍光スペクトルを追加した。その発光は、D4−R6G単量体により近い。
PVDF膜上のRaman色素を評価するために簡単な方法を開発した。第1に、特定の濃度(すなわち1μM)で色素をMeOHに溶解させ、第2に、PVDF膜上に溶媒をドットブロットして乾燥させ、第3に、ブロットの金染色および銀染色を行ってからRamanシグナルを記録する。この純粋色素評価法は、我々がPVDF膜上でのタンパク質定量用に開発したプロトコルに匹敵する。D0−R6G二量体およびD4−R6G単量体の両方のラマンスペクトルを532nmで630nmのレーザーで同一の機器設定(すなわち、共追加(coaddition)を1、積算を10秒間に設定)を用いて記録する。
図4に得られたR6Gの二量体および単量体のSERRSをそれらの安定性に関してさらに試験した。両方のスポットを含有する膜をさらに10日間および30日間にわたり暗所に置いた。両方の日数のSERRSを記載の同一の機器設定下で記録した。図5に示されるとおり、R6G単量体のSERRSシグナルは、徐々に弱くなって10日後に完全に消失したが、R6G二量体のSERRSシグナルは、10日後または30日後まで維持された(ただし、そのシグナルがいくらか強度変化したうえにいくつかの追加のピークが出現したことから、PVDF膜上でのR6G二量体とナノ粒子との特定の相互作用(interation)が示唆されうる)。
Claims (20)
- 有機色素化合物の多量体であって、リンカーを介して共有結合により一体化された少なくとも2分子の有機色素化合物を含む前記多量体。
- 前記多量体が大きいRaman断面積で可視〜近IR領域の光を吸収する、請求項1に記載の多量体。
- 前記有機色素化合物がローダミン6G、クリスタルバイオレット、およびそれらの誘導体よりなる群から選択される、請求項1〜2のいずれかに記載の多量体。
- 前記有機色素化合物が1つ以上の同位体置換に付される、請求項1〜3のいずれかに記載の多量体。
- 前記同位体置換が重水素化である、請求項4に記載の多量体。
- 前記多量体が二量体である、請求項1〜5のいずれかに記載の多量体。
- 前記多量体が三量体または四量体である、請求項1〜5のいずれかに記載の多量体。
- 金属ナノ粒子と請求項1〜7のいずれかに記載の多量体との凝集体。
- 前記金属ナノ粒子が金ナノ粒子または銀ナノ粒子である、請求項8に記載の凝集体。
- 基材と前記基材上に堆積された請求項1〜7のいずれかに記載の多量体とを含む複合材。
- 前記基板上の多量体と凝集させた金属ナノ粒子をさらに含む、請求項10に記載の複合材。
- 前記基材がポリビニリデンフルオリド膜である、請求項10〜11のいずれかに記載の複合材。
- 光学表面用のコーティングであって、請求項1〜7のいずれかに記載の多量体を含む前記コーティング。
- 有機色素化合物のRaman共鳴分光学的シグネチャーを増強する方法であって、前記有機色素化合物の多量体を形成することと、前記多量体をラマン共鳴分光法に付すことと、を含み、前記多量体が、リンカーを介して共有結合により一体化された少なくとも2分子の前記有機色素化合物を含む、前記方法。
- 前記多量体を金属ナノ粒子と凝集させる工程をさらに含む、請求項14に記載の方法。
- 前記金属ナノ粒子が金ナノ粒子または銀ナノ粒子である、請求項15に記載の方法。
- 前記多量体を基材上に堆積させることをさらに含む、請求項14〜16のいずれかに記載の方法。
- 前記基材がポリビニリデンフルオリド膜である、請求項17に記載の方法。
- 前記有機色素化合物がローダミン6G、クリスタルバイオレット、およびそれらの誘導体よりなる群から選択される、請求項14〜18のいずれかに記載の方法。
- 前記有機色素化合物が1つ以上の同位体置換に付される、請求項14〜19のいずれかに記載の方法。
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US20150050743A1 (en) * | 2012-03-23 | 2015-02-19 | Ecole Polytechnique Federale De Lausanne (Epfl) | Method and device for sensing humidity with reversible molecular dimerization |
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WO2011115995A3 (en) | 2012-02-23 |
CN103108921B (zh) | 2015-02-25 |
EP2547732A2 (en) | 2013-01-23 |
US9190099B2 (en) | 2015-11-17 |
EP3360931B1 (en) | 2020-07-01 |
US20130052746A1 (en) | 2013-02-28 |
KR101932038B1 (ko) | 2018-12-26 |
US20160245754A1 (en) | 2016-08-25 |
EP3360931A1 (en) | 2018-08-15 |
US9970878B2 (en) | 2018-05-15 |
CN103108921A (zh) | 2013-05-15 |
EP2547732B1 (en) | 2018-02-28 |
JP5841992B2 (ja) | 2016-01-13 |
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